Title: 10 Best Hotels in Sleepy Hollow, 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)[Sleepy Hollow Car Rentals](https://expedia.ca/Car-Rentals-In-Sleepy-Hollow.d6132427.Car-Rental-Guide)[Sleepy Hollow Vacations](https://expedia.ca/Sleepy-Hollow.d6132427.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 Sleepy Hollow, 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 Sleepy Hollow Spa [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=SPA_ON_SITE) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=APART_HOTEL) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&travelerType=family_friendly) Pool [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=POOL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=HOT_TUB) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=APARTMENT) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=PETS) Condo [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&lodging=CONDO) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Sleepy+Hollow%2C+Chicago%2C+Illinois%2C+United+States+of+America®ionId=6132427&latLong=41.812556%2C-87.740765&adults=2&startDate=2025-11-13&d1=2025-11-13&endDate=2025-11-15&d2=2025-11-15&amenities=WATER_PARK) ## Check prices for these dates Tonight [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-10-30&endDate=2025-10-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=6132427&startDate=2025-10-31&endDate=2025-11-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6132427&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=6132427&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 ## Sleepy Hollow hotels and places to stay ![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) ![Business centre](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/511c43ea.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, 12.7 km from Sleepy Hollow 8.8/10 Excellent (4763) "Great area at a good price. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $134 CA $158 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Magnificent)](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.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) ### Eurostars Magnificent Mile River North, 13 km from Sleepy Hollow 9.0/10 Wonderful (3080) "Excellent stay, close to everything and the staff was super nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kieata CA $167 CA $196 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Chicago - Magnificent Mile Streeterville, 13.4 km from Sleepy Hollow 8.8/10 Excellent (2117) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melinda 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) ![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) ![Fitness facility](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/ada94c01.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) ### Aloft Chicago Mag Mile Streeterville, 13.4 km from Sleepy Hollow 8.6/10 Excellent (2868) "Had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josh 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) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5.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) ![Lake view](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/2866aa1e.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, 14.4 km from Sleepy Hollow 9.4/10 Exceptional (2230) "Rooms were clean with a great view of the lake and the city " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nathan CA $135 CA $206 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/f2c5642d.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/bbeef356.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago The Loop, 11.7 km from Sleepy Hollow 8.4/10 Very good (2271) "Staff was wonderful, property was clean and welcoming. Great amenities for families and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen CA $158 CA $227 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Chicago.h12570.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) ![Exterior](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bb272e60.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) ### citizenM Chicago Downtown Theatre District, 12.7 km from Sleepy Hollow 9.4/10 Exceptional (4026) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sherry CA $159 CA $186 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.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) ![American cuisine](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/fb80c7da.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) ![Daily buffet breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1300000/1293300/1293276/c46ad167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crowne Plaza Chicago West Loop by IHG 10.9 km from Sleepy Hollow 9.0/10 Wonderful (1636) "Staff was friendly upon check in and the premise was very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelan CA $142 CA $167 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Crowne-Plaza-Chicago-West-Loop.h1293276.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) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/e43f096f.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) ### Congress Plaza Hotel The Loop, 11.9 km from Sleepy Hollow 8.0/10 Very good (9631) "Area is great and walkable distance to touring areas. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alejandro CA $131 CA $154 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-Congress-Plaza-Hotel.h6452.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) ![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) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/d24507d4.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) ### Hilton Chicago/Magnificent Mile Suites Streeterville, 13.8 km from Sleepy Hollow 9.0/10 Wonderful (3201) "Overall it was a great place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $153 CA $180 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/17300/17227/b6152ff3.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) ![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) ### Best Western River North Hotel River North, 12.6 km from Sleepy Hollow 7.8/10 Good (1004) "Great stay" ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Bart CA $141 CA $166 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Chicago-Hotels-Best-Western-River-North-Hotel.h17227.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) ![Interior detail](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/cb4330d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago River North, 12.9 km from Sleepy Hollow 8.0/10 Very good (2546) "Very accessible location and amazing staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fatima CA $107 CA $151 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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/b9be2277.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) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile River North, 12.9 km from Sleepy Hollow 8.4/10 Very good (4127) "This hotel had a great location to shopping and several enjoyable restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) laura CA $158 CA $186 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.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) ![Snack bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/c0ded825.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) ![Lobby](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/cc779b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Riu Plaza Chicago Streeterville, 13.2 km from Sleepy Hollow 9.4/10 Exceptional (2688) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Larry William CA $170 CA $239 total includes taxes & fees Nov 23 - Nov 24 [](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/114000000/113780000/113779900/113779814/2b6118c9.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) ### FOUND Hotel Chicago River North River North, 12.6 km from Sleepy Hollow 8.2/10 Very good (296) "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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1305500/1305402/3df6d1fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1305500/1305402/41b8776a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1310000/1305500/1305402/a1af2bc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1310000/1305500/1305402/3a3575cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Regal Inn - Chicago O'Hare Airport 17.1 km from Sleepy Hollow 8.0/10 Very good (1004) "Inexpensive, close to the airport, clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jay CA $85 CA $91 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Chicago-Hotels-Regal-Inn-Chicago-OHare-Airport.h1305402.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/938c3a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/39b9d2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/cc07f74b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/450000/440500/440405/0d409450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Chicago O'Hare Airport 27.1 km from Sleepy Hollow 7.6/10 Good (1483) "I liked that people where super helpful, had its own shuttle and indoor pool" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Valeria CA $97 CA $109 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Chicago-Hotels-Super-8-By-Wyndham-Chicago-OHare-Airport.h440405.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f3b451c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f906be7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/ca3aaed3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/670000/665000/664918/f9eb35b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Suites Chicago O'Hare Airport 18.7 km from Sleepy Hollow 8.2/10 Very good (2718) "Clean quiet and great location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cyrus CA $105 CA $120 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Chicago-Hotels-Comfort-Suites-Schiller-Park-Chicago-OHare-Airport.h664918.Hotel-Information) ![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) ![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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/a23482f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitehall Hotel, BW Premier Collection Streeterville, 13.5 km from Sleepy Hollow 8.2/10 Very good (3665) "Excellent location, old style hotel with an independent feel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose CA $119 CA $139 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Chicago-Hotels-The-Whitehall-Hotel.h17903.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/05f95ad0.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) ### Silversmith Hotel Chicago Downtown Theatre District, 12.2 km from Sleepy Hollow 9.4/10 Exceptional (2030) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl CA $148 CA $216 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.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=2025-11-13&endDate=2025-11-14®ionId=6132427&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Where to stay in Sleepy Hollow Find the best Sleepy Hollow 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 Sleepy Hollow Hotel Reviews ![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) ![Pendry Chicago](//images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg) ### Pendry Chicago 10/10 Excellent "We loved the Pendry!" [](https://expedia.ca/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) ## Frequently asked questions ### What are the best family hotels in Sleepy Hollow? > The [Carlton Inn Midway](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) in Chicago is a fantastic option for families seeking comfort and convenience during their travels. This family-friendly hotel offers complimentary cribs and free stays for children, making it an excellent choice for those traveling with little ones. ### What hotels in Sleepy Hollow offer free breakfast? > [Carlton Inn Midway](https://www.expedia.ca/Chicago-Hotels-Carlton-Inn-Midway.h2949171.Hotel-Information) in Chicago is an excellent choice for travellers seeking a family-friendly atmosphere with convenient amenities. This welcoming hotel offers a complimentary continental breakfast, ensuring that families can start their day off right without any hassle. The 24-hour airport shuttle service makes it easy for guests to navigate their travel plans, great for families arriving with little ones in tow. ### 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 Sleepy Hollow hotel for you. ### How can I save on a Sleepy Hollow hotel booking with Expedia? > Before booking your Sleepy Hollow 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 Sleepy Hollow hotel? > Hotel prices in Sleepy Hollow 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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