Title: The Best Hotels in Sleepy Hollow, Chicago - 2026 Updated Prices | Expedia.co.uk [Holiday Rentals in Chicago](https://expedia.co.uk/Chicago-Holiday-Rentals.d178248.Travel-Guide-HolidayRentals)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Sleepy Hollow Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Sleepy-Hollow.d6132427.Car-Hire-Guide)[Sleepy Hollow Holidays](https://expedia.co.uk/Sleepy-Hollow.d6132427.Holidays-City-Breaks) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Hotels in Sleepy Hollow, Chicago - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Tonight [7 Jan - 8 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6132427&startDate=2026-01-07&endDate=2026-01-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [8 Jan - 9 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6132427&startDate=2026-01-08&endDate=2026-01-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [9 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6132427&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [16 Jan - 18 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=6132427&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Property class ## Our top choices for Sleepy Hollow hotels ![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/10000000/9420000/9418300/9418281/32b602ff.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) ![Cocktail bar](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/2aaf07f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Freehand Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) River North, 8 mi from Sleepy Hollow 8.0/10 Very good (2693) "Great fun place to stay close to most things in downtown " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kayla £60 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Freehand-Chicago.h9418281.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/5bec7925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/dfb99e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/d37889fe.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 [](https://www.expedia.co.uk/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) The Loop, 7.9 mi from Sleepy Hollow 8.8/10 Excellent (4887) "Would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zach £71 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Chicago-Hotels-River-Hotel.h2675313.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/58ac280a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/2ad62276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/693d9c34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 7:00 AM to 10:00 PM, pool loungers](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/352e3b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft Chicago Mag Mile [](https://www.expedia.co.uk/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) Streeterville, 8.3 mi from Sleepy Hollow 8.6/10 Excellent (3014) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisha £72 includes taxes & fees 21 Jan - 22 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.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/w1201h1722x0y78-8f9c452e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/33cb1dae.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 [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) Streeterville, 8.2 mi from Sleepy Hollow 9.4/10 Exceptional (3121) "Second time to stay here, everything is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wei £100 includes taxes & fees 8 Jan - 9 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, City View | City view](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/3e0e58e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/086ff612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Congress Plaza Hotel [](https://www.expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) The Loop, 7.4 mi from Sleepy Hollow 8.0/10 Very good (9780) "Wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zach £72 includes taxes & fees 8 Jan - 9 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/da498d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/2435ca6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/ec33d4f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/580000/570400/570329/0ea4e737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites by Hilton Chicago Downtown Magnificent Mile [](https://www.expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) Streeterville, 8.3 mi from Sleepy Hollow 8.2/10 Very good (2813) "Great hotel staff and location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline £104 includes taxes & fees 14 Jan - 15 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown-Magnificent-Mile.h570329.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/b131add8.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 [](https://www.expedia.co.uk/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) Streeterville, 8.3 mi from Sleepy Hollow 8.8/10 Excellent (2221) "Fantastic stay! Looking forward to staying here again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amber £74 includes taxes & fees 14 Jan - 15 Jan [](https://www.expedia.co.uk/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/6d9bcb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/w3995h2667x0y0-afbbbc14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wade [](https://www.expedia.co.uk/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) Streeterville, 8.6 mi from Sleepy Hollow 8.4/10 Very good (1578) "Easy check in and out, excellent room service and dining menu." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin Bradford £88 includes taxes & fees 12 Jan - 13 Jan [](https://www.expedia.co.uk/Chicago-Hotels-W-Chicago-Lakeshore.h1346.Hotel-Information) ![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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/07c9ead9.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) ![42-inch flat-screen TV with cable channels, TV, pay films](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f5951ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Chicago/Magnificent Mile Suites [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) Streeterville, 8.6 mi from Sleepy Hollow 9.0/10 Wonderful (3671) "Great hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William £78 includes taxes & fees 14 Jan - 15 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/7744cb58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2560x3y3-c4100b4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/d34c171a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (2 Room) | Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/22700/22684/w3837h2561x3y0-7e662cc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Claridge House Chicago, Tapestry Collection by Hilton [](https://www.expedia.co.uk/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information) Gold Coast, 8.6 mi from Sleepy Hollow 9.0/10 Wonderful (1514) "Very nice and quiet, excellent location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony £74 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Claridge-House-Chicago.h22684.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/7923a1d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bc9a17b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed (View) | Premium bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/83000000/82660000/82652400/82652306/bd7c3671.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/83000000/82660000/82652400/82652306/83c82ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Chicago Downtown [](https://www.expedia.co.uk/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) Theatre District, 7.9 mi from Sleepy Hollow 9.4/10 Exceptional (4169) "Stay was great and in a great location!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley £90 includes taxes & fees 29 Jan - 30 Jan [](https://www.expedia.co.uk/Chicago-Hotels-CitizenM-Chicago-Downtown.h82652306.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/b3bac7c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/74cf409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/d4307099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Quarters Hotel Wacker at Michigan, Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) The Loop, 7.9 mi from Sleepy Hollow 8.8/10 Excellent (2047) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kramer £71 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) ![Nightclub](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/0120c0e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed | View from room](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/3ef6d343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/9378ca8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/905f4e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Club Quarters Hotel, Central Loop, Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Club-Quarters-Hotel.h565746.Hotel-Information) Theatre District, 7.3 mi from Sleepy Hollow 8.8/10 Excellent (3368) "Nice Hotel, convenient location fot shopping and walking around" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerima £69 includes taxes & fees 26 Jan - 27 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Club-Quarters-Hotel.h565746.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) ![2 restaurants, breakfast, lunch, dinner served; Latin American cuisine ](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/cadeb422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillow-top beds, in-room safe, desk](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/a68260d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sable at Navy Pier Chicago, Curio Collection by Hilton [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) Streeterville, 8.9 mi from Sleepy Hollow 9.4/10 Exceptional (2326) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela £113 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3840h2559x0y3-c577bf94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2560x3y0-ce2754d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/fb110cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Lake View | Premium bedding, pillow-top beds, in-room safe, desk](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 [](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) The Loop, 8 mi from Sleepy Hollow 9.4/10 Exceptional (3452) "The Hotel was amazing great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donnisha £147 includes taxes & fees 20 Jan - 21 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/f36e2ebe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/66eb210e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d288265e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/dec7b24e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.Hotel-Information) River North, 8 mi from Sleepy Hollow 8.6/10 Excellent (4330) "Amazing staff and perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandi £68 includes taxes & fees 14 Jan - 15 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Hilton-Garden-Inn-Chicago-DowntownMagnificent-Mile.h424187.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) ![Suite (Magnificent) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/53a89031.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/afa1818a.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) ### Eurostars Magnificent Mile [](https://www.expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) River North, 8.1 mi from Sleepy Hollow 9.0/10 Wonderful (3169) "Clean, nicely priced, nice staff, and perfectly located to food and nightlife " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Calvin £81 includes taxes & fees 5 Feb - 6 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/098ab5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/w3837h2557x3y3-19dabd9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed (Millennium - ADA) | In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/6822e14c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Arlo Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Julian.h26910691.Hotel-Information) Theatre District, 7.8 mi from Sleepy Hollow 9.4/10 Exceptional (1926) "Clean and comfy room, friendly staff, great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Agata £112 includes taxes & fees 10 Jan - 11 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Hotel-Julian.h26910691.Hotel-Information) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18000/17903/fd235ec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitehall Hotel, BW Premier Collection [](https://www.expedia.co.uk/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) Streeterville, 8.4 mi from Sleepy Hollow 8.2/10 Very good (3853) "great location" ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Isabel £62 includes taxes & fees 12 Jan - 13 Jan [](https://www.expedia.co.uk/Chicago-Hotels-The-Whitehall-Hotel.h17903.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/34f4da65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/6f539c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25500/25452/a9fdeea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Warwick Allerton - Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.Hotel-Information) Streeterville, 8.3 mi from Sleepy Hollow 8.6/10 Excellent (3016) "Every thing is perfect, the location, safe for solo travel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken £68 includes taxes & fees 23 Jan - 24 Jan [](https://www.expedia.co.uk/Chicago-Hotels-Warwick-Allerton-Chicago.h25452.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.co.uk/Hotel-Search?startDate=2026-01-21&endDate=2026-01-22®ionId=6132427&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Where to stay in Sleepy Hollow Find the best Sleepy Hollow areas for the activities you enjoy most. - Downtown Chicago - Magnificent Mile - The Loop - River North - Theatre District ![Downtown Chicago featuring 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 showing 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 which includes 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 which includes signage and a city](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.co.uk/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.co.uk/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 which includes 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 showing 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 which includes a city, a hotel and skyline](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.co.uk/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 Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. [See properties](https://www.expedia.co.uk/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 showing a ferry and a river or creek](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.co.uk/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 Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. [See properties](https://www.expedia.co.uk/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 featuring street scenes, cbd and a city](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 which includes central business district, street scenes and a city](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.co.uk/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 Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city. [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=6350695) ![Chicago which includes rides](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23717-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Chicago showing landscape views, skyline and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23710-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Chicago showing theatre scenes, night scenes and street scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23730-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Frank Lloyd Wright Home and Studio which includes a house and interior views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/26000/26627-Frank-Lloyd-Wright-Home-And-Studio.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) ![Chicago which includes night scenes, rides and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23718-Chicago.jpg?impolicy=fcrop&w=960&h=540&p=1&q=medium) [](https://www.expedia.co.uk/Hotel-Search?pwaOverlay=map®ionId=651190586167894016) ![Theatre District map](https://maps.googleapis.com/maps/api/staticmap?&size=289x340&map_id=c017d89749dc74ad&markers=icon:%7C&path=enc:mxs%7EF%7E%7EzuOa%40wb%40mAwCKcDmHiMl%7B%40MZry%40_o%40v%40&key=AIzaSyAoVHdVOa5-BDRxGhFoAHYIHPst1T09Jo0&signature=wPQBnQtd4sat1wXcy-Q0SbgXS1s=) ### Theatre District While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line). [See properties](https://www.expedia.co.uk/Hotel-Search?regionId=651190586167894016) ## Top Sleepy Hollow Hotel Reviews ![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 "Great hotel " [](https://expedia.co.uk/Chicago-Hotels-LondonHouse-Chicago.h12786616.Hotel-Information) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg) ### Club Quarters Hotel Wacker at Michigan, Chicago 10/10 Excellent "Everything was awsome" [](https://expedia.co.uk/Chicago-Hotels-Club-Quarters-Hotel.h889753.Hotel-Information) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg) ### Silversmith Hotel Chicago Downtown 10/10 Excellent "Everything was good and the staff was friendly " [](https://expedia.co.uk/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg) ### Pendry Chicago 10/10 Excellent "Everything was exceptional!!!!!" [](https://expedia.co.uk/Chicago-Hotels-Pendry-Chicago.h982552.Hotel-Information) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg) ### Palmer House a Hilton Hotel 10/10 Excellent "What stood out from Palmers house hotel for me was how spacious the rooms were! I got a 2 bed for 4 guests and we all fit perfectly with luggage and all , everyone accommodated easily :) " [](https://expedia.co.uk/Chicago-Hotels-Palmer-House-A-Hilton-Hotel.h8079.Hotel-Information) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg) ### Embassy Suites by Hilton Chicago Downtown River North 10/10 Excellent "Yes" [](https://expedia.co.uk/Chicago-Hotels-Embassy-Suites-Chicago-Downtown.h11580.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 "Brianna was really nice. I traveled here on the solo trip for Christmas. She gave me great recommendations and overall, she was just friendly every day I went down to the lobby. " [](https://expedia.co.uk/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg) ### Swissotel - Chicago 10/10 Excellent "Everything was perfect from the room to the service and location. Definitely a great option when you visit Chicago " [](https://expedia.co.uk/Chicago-Hotels-Swissotel-Chicago.h17288.Hotel-Information) ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg) ### Sable at Navy Pier Chicago, Curio Collection by Hilton 10/10 Excellent "It was incredible! Service, room, and overall hotel were 10/10!" [](https://expedia.co.uk/Chicago-Hotels-Sable-At-Navy-Pier-Chicago.h57651125.Hotel-Information) ## Frequently asked questions ### What are the best family hotels in Sleepy Hollow? ### What hotels in Sleepy Hollow offer free breakfast? ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Sleepy Hollow hotel booking with Expedia? ### How much is the nightly rate at a Sleepy Hollow hotel? ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Other - More ways to book - [5 Star Hotels in New City ](https://www.expedia.co.uk/5Star-New-City-Chicago-Hotels.s50-n6132388-0.Travel-Guide-Filter-Hotels) - [Hotels near Anna and Frederick Douglass Park ](https://www.expedia.co.uk/Anna-And-Frederick-Douglass-Park-Hotels.0-l507384-0.Travel-Guide-Filter-Hotels) - [Ashburn Hotels ](https://www.expedia.co.uk/Ashburn-Chicago-Hotels.0-n6132369-0.Travel-Guide-Filter-Hotels) - [Austin Hotels ](https://www.expedia.co.uk/Austin-Chicago-Hotels.0-n6132238-0.Travel-Guide-Filter-Hotels) - 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Peter and Paul Church ](https://www.expedia.co.uk/SS-Peter-And-Paul-Church-McKinley-Park.d6247219.Attraction) - [Visit Summit ](https://www.expedia.co.uk/Summit.dx177671) - [Rental cars Midway Intl. airport ](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Midway-Intl.d5719117.Car-Hire-Guide) - [Enterprise Rental Cars in Southwest Side ](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Southwest-Side.d553248635976475403-c15.Car-Rental-Guide-Suppliers) - [Things to do in Stickney ](https://www.expedia.co.uk/Things-To-Do-In-Stickney.d6132201.Travel-Guide-Activities) - [Book Hotels in Sleepy Hollow on Expedia.com ](https://www.expedia.com/Sleepy-Hollow-Chicago-Hotels.0-n6132427-0.Travel-Guide-Filter-Hotels)