Title: 10 Best Hotels in Oakland, Chicago for 2025 | Expedia.ca [Vacation Rentals in Chicago](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6132392.Car-Rental-Guide)[Oakland Vacations](https://expedia.ca/Oakland.d6132392.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Hotels in Oakland, Chicago - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Oakland Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&travelerType=family_friendly) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&lodging=APART_HOTEL) Spa [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&amenities=SPA_ON_SITE) Pool [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&amenities=POOL) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&lodging=APARTMENT) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&amenities=HOT_TUB) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&amenities=WATER_PARK) Condo [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&lodging=CONDO) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Oakland%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132392&latLong=41.823816%2C-87.602689&adults=2&startDate=2025-11-15&d1=2025-11-15&endDate=2025-11-17&d2=2025-11-17&amenities=PETS) ## Check prices for these dates Tonight [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 1 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Oakland hotels and places to stay ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, down comforters](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/06b28362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/e69bed89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile River North, 8.1 km from Oakland 9.0/10 Wonderful (3087) "Awesome location and excellent service, the staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Salvador CA $162 CA $190 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e85c42c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Single Beds](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/6d4883c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Hotel The Loop, 7.4 km from Oakland 8.8/10 Excellent (4766) "Great area at a good price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $166 CA $195 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Streeterville, 7.9 km from Oakland 8.6/10 Excellent (2870) "Staff are nice, room was clean. Enjoyed the lobby, pool table and bar. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily CA $151 CA $177 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Chicago - Magnificent Mile Streeterville, 7.8 km from Oakland 8.8/10 Excellent (2121) "Convenient location, over all cleanliness and staff was exceptional." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) AMANDA CA $144 CA $169 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Streeterville, 7.5 km from Oakland 9.4/10 Exceptional (2231) "Great hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gilles CA $135 CA $207 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/1792d463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 20.00 per person)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/8967eebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Chicago Downtown Theatre District, 7.3 km from Oakland 9.4/10 Exceptional (4037) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Riley CA $160 CA $187 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago River North, 7.9 km from Oakland 8.0/10 Very good (2552) "Location was excellent would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julio CA $108 CA $152 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/5e299c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/18c5ca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile River North, 7.8 km from Oakland 8.4/10 Very good (4127) "We definitely will stay there again place was very nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy CA $149 CA $174 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/172457c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites Streeterville, 8.6 km from Oakland 9.0/10 Wonderful (3211) "Overall it was a great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $150 CA $176 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, City View | Living area](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/cc919354.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, 1 King Bed, Lake View, Lakeside](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e932b9a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Congress Plaza Hotel The Loop, 6 km from Oakland 8.0/10 Very good (9641) "Excellent location very convenient parking nice staff clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike CA $131 CA $154 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Living area](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b812d0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/b5bf3aa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago The Loop, 5.7 km from Oakland 8.4/10 Very good (2272) "Great Hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luz CA $159 CA $227 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f7f78ace.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/f9eed5f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/520a670b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 2 Double Beds, Non Smoking, Refrigerator (with Sofabed)](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/aeb6fede.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western River North Hotel River North, 8 km from Oakland 7.8/10 Good (1005) "It was a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brooklynn CA $141 CA $166 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/2f70f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/f5c52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Riu Plaza Chicago Streeterville, 7.9 km from Oakland 9.4/10 Exceptional (2693) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larry William CA $158 CA $226 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/cbeee5a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/0c9aebe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/9ab0dcf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/114000000/113780000/113779900/113779814/68145d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FOUND Hotel Chicago River North River North, 8.1 km from Oakland 8.2/10 Very good (299) "Perfect location! Tons of restaurants and shopping nearby! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MaryJane CA $106 CA $125 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Chicago-Hotels-FOUND-Hotel-Chicago.h113779814.Hotel-Information) ![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/f9d27fb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/5b3c70b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/871940a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/fb80c7da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Chicago West Loop by IHG 7.3 km from Oakland 9.0/10 Wonderful (1638) "Great Hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cesar CA $143 CA $167 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/dd081548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/ddbd86a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, free cribs/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/64c4029a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG River North, 7.7 km from Oakland 8.8/10 Excellent (3292) "The room was beautiful the view was exquisite the staff was friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juanita CA $136 CA $159 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Voco-Chicago-Downtown.h76459163.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/b573f792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/d5770f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/891da469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2510000/2506500/2506471/b4d2cc05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Chicago Downtown The Loop, 7 km from Oakland 8.6/10 Excellent (2593) "Very nice for price and location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $137 CA $186 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Chicago-Downtown.h2506471.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/b0f5bd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/c5cac7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silversmith Hotel Chicago Downtown Theatre District, 6.7 km from Oakland 9.4/10 Exceptional (2031) "Great location, friendly staff , comfy bed and overall very comfortable room! Would stay here again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tracy CA $140 CA $207 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/af0ef9e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/w3576h2561x0y0-5f9110d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/c12c78f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/10000000/9070000/9069700/9069667/0ec157ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric The Loop Chicago Theatre District, 6.7 km from Oakland 9.0/10 Wonderful (2225) "Probably my favorite place to stay in the Loop." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $173 CA $203 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Hyatt-Centric-The-Loop-Chicago.h9069667.Hotel-Information) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Theatre District, 6.7 km from Oakland 8.4/10 Very good (2055) "Wonderful historic property, we loved our stay in this beautiful hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $153 CA $215 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16®ionId=6132392&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Hotels in Oakland with free breakfast ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/55a8ba7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/5d460cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a9c979ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Streeterville, 7.5 km from Oakland - Breakfast included 9.4/10 Exceptional (2231) CA $135 CA $207 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-25&endDate=2025-11-26&selected=57651125&PinnedHotelID=57651125&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2695x3y3-e619dd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/4df3bcb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Lake View](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2561x3y0-ec3252d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Chicago The Loop, 7.3 km from Oakland - Breakfast included 9.4/10 Exceptional (3376) CA $201 CA $277 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=4903&PinnedHotelID=4903&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/9d783fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/8318473d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/aaad0ec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Palmer House a Hilton Hotel Theatre District, 6.7 km from Oakland - Breakfast included 8.4/10 Very good (2055) CA $153 CA $215 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/943262bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner, brunch served; American cuisine ](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/e47956bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade Streeterville, 7.9 km from Oakland - Breakfast included 8.4/10 Very good (1402) CA $155 CA $182 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=1346&PinnedHotelID=1346&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![Cocktail bar](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/56c2d84c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/50be090a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile Streeterville, 7.9 km from Oakland - Breakfast included 8.6/10 Excellent (2870) CA $151 CA $177 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=26998765&PinnedHotelID=26998765&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![Front of property](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/2f70f55e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/f5c52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Riu Plaza Chicago Streeterville, 7.9 km from Oakland - Breakfast included 9.4/10 Exceptional (2693) CA $158 CA $226 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-25&endDate=2025-11-26&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![Reception](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e85c42c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Single Beds](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/6d4883c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/e50ef89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Hotel The Loop, 7.4 km from Oakland - Breakfast included 8.8/10 Excellent (4766) CA $166 CA $195 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-12&endDate=2025-11-13&selected=2675313&PinnedHotelID=2675313&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c8177aa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/a23482f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/8750140b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitehall Hotel, BW Premier Collection Streeterville, 8.6 km from Oakland - Breakfast included 8.2/10 Very good (3669) CA $119 CA $140 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=17903&PinnedHotelID=17903&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b1113923.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/d7ae47e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/8e39b688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Chicago - Magnificent Mile Streeterville, 7.8 km from Oakland - Breakfast included 8.8/10 Excellent (2121) CA $144 CA $169 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=21152&PinnedHotelID=21152&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) ![Terrace/patio](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, City View | View from room](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/c06f4b61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/1792d463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily buffet breakfast (USD 20.00 per person)](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/8967eebd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Chicago Downtown Theatre District, 7.3 km from Oakland - Breakfast included 9.4/10 Exceptional (4037) CA $160 CA $187 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20&selected=82652306&PinnedHotelID=82652306&HadPinnedHotel=true®ionId=6132392&adults=2&mealPlan=FREE_BREAKFAST&openPlayBack=true) [See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16®ionId=6132392&adults=2&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## Hotels in Oakland with a pool ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/2806d344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/481e5f5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/a07d9bd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5500/5467/9cc7a10c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Chicago Dwtn - The Mart by IHG River North, 7.7 km from Oakland - Pool 8.8/10 Excellent (1982) CA $136 CA $159 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=5467&PinnedHotelID=5467&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/5e299c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/59baefbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/18c5ca41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile River North, 7.8 km from Oakland - Pool 8.4/10 Very good (4127) CA $149 CA $174 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=424187&PinnedHotelID=424187&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Breakfast and lunch served](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/120d903c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/7705f099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/5dd90c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Chicago Magnificent Mile Streeterville, 7.9 km from Oakland - Pool 8.8/10 Excellent (1556) CA $154 CA $181 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=982517&PinnedHotelID=982517&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/e1eb307d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/fa7d1870.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/eaff657c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Royal Sonesta Chicago River North River North, 7.8 km from Oakland - Pool 9.2/10 Wonderful (2213) CA $154 CA $225 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=3023837&PinnedHotelID=3023837&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Pool](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/d5b5d773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/fe59f9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/0f103d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33690000/33682500/33682469/6dc8c836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown South Loop The Loop, 5.4 km from Oakland - Pool 8.8/10 Excellent (1699) CA $130 CA $152 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=33682469&PinnedHotelID=33682469&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/4c0ebbe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/e436fe11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/311c65a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, Netflix, pay movies, streaming services](https://images.trvl-media.com/lodging/1000000/20000/12200/12167/edeb1954.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Grand Chicago Riverwalk Streeterville, 7.4 km from Oakland - Pool 8.4/10 Very good (1548) CA $222 CA $303 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=12167&PinnedHotelID=12167&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Indoor pool, seasonal outdoor pool, free cabanas, sun loungers](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8de272e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/f5341c22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/d70c748e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Radisson Blu Aqua Hotel Chicago 7.1 km from Oakland - Pool 8.6/10 Excellent (1746) CA $196 CA $266 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=4520626&PinnedHotelID=4520626&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Exterior](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/86b2dc93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/289caf93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/0d2b3bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tapas bar](https://images.trvl-media.com/lodging/2000000/1120000/1110100/1110039/e6c4a358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotels by Marriott Chicago Downtown River North, 8 km from Oakland - Pool 8.8/10 Excellent (1005) CA $152 CA $179 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=1110039&PinnedHotelID=1110039&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/9b9a583c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1faa6c2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/0a522c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown River North River North, 8 km from Oakland - Pool 8.6/10 Excellent (5180) CA $165 CA $194 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) ![Exterior](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/57098577.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/w3837h2557x3y3-b429e995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/2dfdebf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed (Specialty)](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/5a3c23ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Chicago/Downtown - The Loop The Loop, 7.1 km from Oakland - Pool 8.8/10 Excellent (1092) CA $154 CA $181 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-25&endDate=2025-11-26&selected=11062225&PinnedHotelID=11062225&HadPinnedHotel=true®ionId=6132392&adults=2&amenities=POOL&openPlayBack=true) [See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16®ionId=6132392&adults=2&sort=RECOMMENDED&amenities=POOL&openPlayBack=true) ## Top guest rated hotels in Oakland ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/c14e1876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/5132819a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago River North, 7.9 km from Oakland 8.0/10 Very good (2552) CA $108 CA $152 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-30&endDate=2025-12-01&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![Bar (on property)](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/6b27f192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/dd081548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/ddbd86a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, free cribs/infant beds](https://images.trvl-media.com/lodging/77000000/76460000/76459200/76459163/64c4029a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### voco Chicago Downtown - Riverwalk by IHG River North, 7.7 km from Oakland 8.8/10 Excellent (3292) CA $136 CA $159 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-24&endDate=2025-11-25&selected=76459163&PinnedHotelID=76459163&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/43039f7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/22cb8b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/ccacdd84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago Magnificent Mile, 8.1 km from Oakland 8.4/10 Very good (2944) CA $123 CA $186 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=25452&PinnedHotelID=25452&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![Room, 1 King Bed, Corner](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2249x3y0-2724cf53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3837h2496x3y3-f9e98aea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/w3840h2557x0y3-a19ef5e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151200/151139/461957e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Chicago Magnificent Mile Streeterville, 8 km from Oakland 9.0/10 Wonderful (1029) CA $154 CA $222 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=151139&PinnedHotelID=151139&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/b0f5bd1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/04b62050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/c5cac7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Silversmith Hotel Chicago Downtown Theatre District, 6.7 km from Oakland 9.4/10 Exceptional (2031) CA $140 CA $207 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-27&endDate=2025-11-28&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d46a8a4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/9097f753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view from property](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/2b1c0fd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, in-room safe](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/279c3768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Felix River North/Magnificent Mile River North, 8.3 km from Oakland 8.2/10 Very good (2327) CA $98 CA $158 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-25&endDate=2025-11-26&selected=2222364&PinnedHotelID=2222364&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![Ballroom](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/0030a761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/172457c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites Streeterville, 8.6 km from Oakland 9.0/10 Wonderful (3211) CA $150 CA $176 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-17&endDate=2025-11-18&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/ab309a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/19390ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, alfresco dining, open daily](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/df696474.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/8000000/7070000/7063300/7063210/a073ef3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Chicago River North, 8.3 km from Oakland 8.6/10 Excellent (1933) CA $136 CA $193 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-25&endDate=2025-11-26&selected=7063210&PinnedHotelID=7063210&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/6ec8820c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/c7c0b5b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2560x3y3-e49910c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claridge House Chicago, Tapestry Collection by Hilton Gold Coast, 9.3 km from Oakland 9.0/10 Wonderful (1409) CA $114 CA $174 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-10&endDate=2025-11-11&selected=22684&PinnedHotelID=22684&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) ![Exterior](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501235/w3837h2556x3y3-5469aeb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King, Room, Accessible | Living area](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501235/w3837h2556x3y4-42aed1d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds (Drinks & Snacks)](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501235/w3836h2556x4y4-2f6224e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501235/w3840h2556x0y4-3c48c376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown Riverwalk Theatre District, 7.3 km from Oakland 9.0/10 Wonderful (1933) CA $150 CA $176 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&selected=11501235&PinnedHotelID=11501235&HadPinnedHotel=true®ionId=6132392&adults=2&guestRating=35&openPlayBack=true) [See more properties](https://www.expedia.ca/Hotel-Search?startDate=2025-11-15&endDate=2025-11-16®ionId=6132392&adults=2&sort=RECOMMENDED&guestRating=35&openPlayBack=true) ## Where to stay in Oakland Find the best Oakland areas and neighborhoods for the activities you enjoy most. - Downtown Chicago - Magnificent Mile - The Loop - River North - Lincoln Park ![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191755-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Downtown Chicago which includes a high-rise building and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332087-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Downtown Chicago featuring signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332073-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Downtown Chicago featuring a city and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332084-Downtown-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=6350699) ![Downtown Chicago map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:uxq%7EFvjavOurAq%40mA%7DgDuTtO%7BFzJuOr%40mk%40z_%40MifBum%40%7EAGmaAx%7EAopCna%40uM%7EoC%7C%7DAx%40%7CkCnk%40yAy%40n%7B%40gt%40dE%7Bg%40pFo%40%60%7EB&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=XpzTv33-iXOpq3icViGLtz3e_jE=) ### Downtown Chicago The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. [See properties](https://www.expedia.ca/Hotel-Search?regionId=6350699) ![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543374-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Magnificent Mile - River North showing signage and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191832-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Magnificent Mile - River North which includes street scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191836-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Magnificent Mile - River North showing a hotel, a city and modern architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24572-Magnificent-Mile.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=800025) ![Magnificent Mile map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:gnt%7EF%60dyuOugAK%3FcChgALJ%60C&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=eJaOW3wrdH9kguwKvLeM9_7UbMs=) ### Magnificent Mile Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service. [See properties](https://www.expedia.ca/Hotel-Search?regionId=800025) ![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543387-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543370-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![The Loop - Downtown featuring a river or creek and a ferry](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191752-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192010-The-Loop-Downtown.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=800024) ![The Loop map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:syr%7EFxx%7BuOqa%40mAeEqK_%40sp%40kG%7BKvAwg%40Xok%40%7C_%40x%40xF%7EPtlAi%40dCh%40DzOxDxCDnbBkNr%40e%5E%7EEkKzGiVfC&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=XwfHKgKFqor-NvwNZdw8nZOnNbI=) ### The Loop Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago. [See properties](https://www.expedia.ca/Hotel-Search?regionId=800024) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543384-chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Shops at North Bridge which includes central business district, a city and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191962-Shops-At-North-Bridge.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191756-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Shops at North Bridge showing a city, central business district and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191961-Shops-At-North-Bridge.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=6350695) ![River North map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:%7B%7Cu%7EFl_%7DuOWcpA%7CECQ%7Db%40xi%40w%40nGbNJ%7Ep%40xCbHxAdBcB%7ECuAhA%7DKdCyGvFiGdDsD%7CDeCzEwBfBoN%5E&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=pVk_WdkeHd9iD-9kitVtoqcFN2A=) ### River North Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building. [See properties](https://www.expedia.ca/Hotel-Search?regionId=6350695) ![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24578-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Lincoln Park Zoo showing autumn colours and signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26661-Lincoln-Park-Zoo.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24579-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Chicago History Museum featuring interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24583-Chicago-History-Museum.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.ca/Hotel-Search?pwaOverlay=map®ionId=6059328) ![Lincoln Park map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:u%7E%7C%7EFhscvO%40%7DMjAWEyE_JFsDaCAl%40qDD%3F%7DBjU_%40AkAiAQ%40aWbAKAyFqALQeJzAIKaNiAJOgUTi%40%7E%40KEgF_BD%3FuMbBMc%40_NiAAI%7DImAIKmB%7CAQMeVxAKQ%7BOwGaCnCQHeCtBKFgC%7DAUSaGbBIx%40i%60Axp%40mMbD%7EGpa%40%7DJpR%7DM%60NgVzGrLV%60n%40mJ%7EEh%40%60AfIKClIuCNp%40xRrBWl%40b%7EAoEJoElF%7CArEjIiGKpNoVzJqItQvCfKsArA%7DL%60FuXhVm%40%60NaKhR%7BK%7CAcFbKiAzFsK_MqLbN%7DAJ&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=KktfaLNeQ_9ZFVphttKdls3N5TA=) ### Lincoln Park Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads. [See properties](https://www.expedia.ca/Hotel-Search?regionId=6059328) ## Top Oakland Hotel Reviews ![InterContinental Chicago Magnificent Mile by IHG](//images.trvl-media.com/lodging/1000000/30000/20300/20205/35cb1bb8_y.jpg) ### InterContinental Chicago Magnificent Mile by IHG 10/10 Excellent "Your pool was AMAZING. I had so much fun in your hotel with my mom. A kind worker let my mom and I microwave our ramen which was really kind of him. Your bed was so comfy, the bathroom shower was GREAT. THANKYOU SO MUCH" [](https://expedia.ca/Chicago-Hotels-InterContinental-Chicago-Magnificent-Mile.h20205.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](//images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "i have been visiting chicago frequently over the last few months and this hotel thus far has exceeded any hotel stay that ive had. the staff was amazing and the location and room was great for the money spent. i will return " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![citizenM Chicago Downtown](//images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/55b627dd_y.jpg) ### citizenM Chicago Downtown 10/10 Excellent "Closer parking or vale" [](https://expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![The Whitehall Hotel, BW Premier Collection](//images.trvl-media.com/lodging/1000000/20000/18000/17903/daaf5f2e_y.jpg) ### The Whitehall Hotel, BW Premier Collection 10/10 Excellent "Staff was very nice and the hotel is near everything " [](https://expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](//images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "Floor-to- ceiling windows providing beautiful views of the Lake and City skyline (and windowseat) were very nice. Location was nice. Room was quiet. Bed was very comfortable. Staff was courteous and helpful." [](https://expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![Warwick Allerton - Chicago](//images.trvl-media.com/lodging/1000000/30000/25500/25452/w1261h711x0y1-96bd53d1_y.jpg) ### Warwick Allerton - Chicago 10/10 Excellent "Computers need updates. Staff great." [](https://expedia.ca/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) ![Congress Plaza Hotel](//images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Great" [](https://expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![The Royal Sonesta Chicago Downtown](//images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "The only negative experience was seeing the Disgraceful Trump Tower across the street. " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![Hotel Riu Plaza Chicago](//images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "Breakfast was great, staff is always amazing. Only place I like staying in Chicago!" [](https://expedia.ca/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Oakland that travellers recommend? > [Sophy Hyde Park](https://www.expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) is a standout hotel located in the vibrant city of Chicago, boasting an exceptional score of 9.6. Guests appreciate its blend of modern luxury and historical charm, with high-end amenities such as premium bedding, customized bathrobes, and a stunning terrace great for relaxation. The hotel's prime location in the Historical District allows easy access to local attractions, making it an ideal choice for couples seeking a romantic getaway or travellers looking to explore the city's rich culture. > > > > For families, the [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) shines with a rating of 8.8. Its spacious rooms feature sofa beds and cribs, ensuring comfort for all ages. The hotel offers a complimentary buffet breakfast, making mornings straightforward. Kids will love the indoor pool, while parents can enjoy the 24-hour fitness facilities. The family-friendly atmosphere is enhanced by the option for kids' meals, allowing everyone to dine happily together. ### What hotels in Oakland offer free breakfast? > [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) is a fantastic option for families visiting Chicago. Rated 8.8 by guests, this hotel offers a complimentary buffet breakfast, ensuring that everyone starts the day off right. With an indoor pool, kids can splash around while parents unwind, making it a great spot for family fun. ### What are the best budget hotels in Oakland? > [Hyatt Place Chicago-South/University Medical Center](https://www.expedia.ca/Chicago-Hotels-Hyatt-Place-Chicago-SouthUniversity-Medical-Center.h6059069.Hotel-Information) is an excellent budget-friendly option for families visiting Chicago. This hotel boasts a spacious indoor pool, which is great for kids to splash around while parents relax nearby. Guests appreciate the complimentary breakfast, featuring a delightful buffet that caters to various tastes, ensuring the whole family starts their day right. ### What are the most romantic hotels in Oakland for couples? > For couples seeking a romantic getaway in Oakland, [Sophy Hyde Park](https://www.expedia.ca/Chicago-Hotels-Sophy-Hyde-Park.h22355297.Hotel-Information) is an exceptional choice, boasting a stellar rating of 9.6. This hotel is situated in a charming historical district, enveloping guests in a special environment that melds history with modern comforts. ### Can I cancel my hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Oakland hotel for you. ### How can I save on a Oakland hotel booking with Expedia? > Before booking your Oakland hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia. ### How much is the nightly rate at a Oakland hotel? > Hotel prices in Oakland often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. 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