Title: Book the Best BOUTIQUE Hotels in Oakland in 2026 | 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://a.travel-assets.com/travel-assets-manager/bex-affinities/boutique.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/boutique.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 ## Check availability on Oakland Boutique Hotels Tonight [Jan 31 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2026-01-31&endDate=2026-02-01&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 1 - Feb 2](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2026-02-01&endDate=2026-02-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6132392&startDate=2026-02-13&endDate=2026-02-15&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Oakland boutique hotels ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/11ef5a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/c911ce8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fd235ec7.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) ### The Whitehall Hotel, BW Premier Collection [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) Downtown Chicago 8.2/10 Very good (3,927 reviews) "Location, breakfast was good, room was nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Traci CA $100 CA $117 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/37fa1971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/99cc20aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/e3571b7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21700/21619/67428c96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chicago Hotel Collection - Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) Downtown Chicago 7.6/10 Good (1,192 reviews) "Clean, great customer service, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arturo CA $121 CA $142 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Audrey.h21619.Hotel-Information) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/220cf128.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/3c43769a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/ab84c92e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/886400/886306/5e20364f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ACME Hotel Chicago, Outset Collection by Hilton [](https://www.expedia.ca/Chicago-Hotels-ACME-Hotel-Company.h886306.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (1,941 reviews) "Very convenient place to stay friendly and helpful staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rick CA $110 CA $129 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Chicago-Hotels-ACME-Hotel-Company.h886306.Hotel-Information) ![Reception hall](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/a08df61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/afa1818a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) Downtown Chicago 9.0/10 Wonderful (3,206 reviews) "Hotel staff are nice and the rooms are clean .. This hotel is close to everything , highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria Rochelle CA $118 CA $138 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/b975595d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/c5557162.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/85922bc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, brunch served; Regional cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/30000/21200/21142/b2a072ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel [](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) Downtown Chicago 9.6/10 Exceptional (1,160 reviews) "Wonderful staff, close to number of attractions " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raju CA $126 CA $148 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Blake.h21142.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9c44ca76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/9833019f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/612465b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/6000000/5210000/5204900/5204897/325381ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ivy Boutique Hotel [](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information) Downtown Chicago 8.6/10 Excellent (1,081 reviews) "I always stay here when in town. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $102 CA $120 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Chicago-Hotels-Ivy-Boutique-Hotel.h5204897.Hotel-Information) ![Nightclub](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/6f853099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/95d7089e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/d0c2944a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2160000/2151900/2151878/1893647b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Central Loop Hotel [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) Downtown Chicago 8.6/10 Excellent (2,009 reviews) "Great room, wonderful and helpful happy staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dr. Burt CA $145 CA $170 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Chicago-Hotels-Central-Loop-Hotel.h2151878.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/cbe9b050.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) ![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) ### Hotel Felix River North/Magnificent Mile [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) Downtown Chicago 8.2/10 Very good (2,541 reviews) "I liked the hotel. The staff was very courteous and friendly. The room was cute. The location is fantastic." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Equilla CA $82 CA $138 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Chicago-Hotels-Hotel-Felix-Chicago.h2222364.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/f57ccf79.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) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3030000/3023900/3023837/20c3f16a.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) ### The Royal Sonesta Chicago River North [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information) Downtown Chicago 9.2/10 Wonderful (2,428 reviews) "Room was perfect, the staff was so friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $144 CA $213 total includes taxes & fees Feb 12 - Feb 13 [](https://www.expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-River-North.h3023837.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/19985e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/48e8b586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bbf9e380.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/a6de8b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staypineapple, An Iconic Hotel, The Loop [](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.Hotel-Information) Downtown Chicago 9.4/10 Exceptional (1,003 reviews) "Location was great, staff was very friendly, and the rooms were clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $156 CA $224 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Chicago-Hotels-Staypineapple.h284792.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=2026-02-14&endDate=2026-02-15®ionId=6132392&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Oakland Hotel Reviews ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Amazing overall will be my go to every trip to Chicago " [](https://expedia.ca/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg) ### The Wade 10/10 Excellent "Lovely room, beautiful hotel, wonderful staff, ideal location to navy pier & Michigan Ave. " [](https://expedia.ca/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/9a897fc5_y.jpg) ### River Hotel 10/10 Excellent "What great value i found at the River. Spotless room, friendly and attentive staff. Can't wait to return!" [](https://expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "2nd time at hotel and will come again. " [](https://expedia.ca/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "We arrived later than planned due to the weather, but the front desk staff greeted us warmly and made us feel welcome right away. They were very friendly and kind. As always, the room was clean this has been consistent every time we stay. The bed and pillows were comfortable, and I absolutely loved the shower. Overall, it’s an all-around great hotel, and we always enjoy our stay here." [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Clean room, great staff, great location " [](https://expedia.ca/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Excellent " [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/74c2f40d_y.jpg) ### LondonHouse Chicago, Curio Collection by Hilton 10/10 Excellent "Beautiful hotel, stunning views, excellent location, amazing staff, and phenomenal rooftop! " [](https://expedia.ca/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "My stay was truly amazing. Thank you and appreciate the hotel hospitality" [](https://expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Oakland? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - More ways to book - [Boutique Hotels in Armour Square ](https://www.expedia.ca/Armour-Square-Chicago-Hotels-Boutique-Hotel.0-n6132365-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Armour Square ](https://www.expedia.ca/Armour-Square-Chicago-Hotels-Cheap-Hotels.0-n6132365-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Armour Square ](https://www.expedia.ca/Armour-Square-Chicago-Hotels-Historic-Hotel.0-n6132365-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Armour Square ](https://www.expedia.ca/Armour-Square-Chicago-Hotels-LGBT-Friendly-Hotel.0-n6132365-0-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Armour Square Hotels ](https://www.expedia.ca/Armour-Square-Chicago-Hotels.0-n6132365-0.Travel-Guide-Filter-Hotels) - 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