Chicago Hotel Guide. Hotels in Sleepy Hollow, Chicago, United States of America
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Our top choices for Sleepy Hollow hotels
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3483)
"Great place to stay "
RaShawna
The price is €81
includes taxes & fees
8 Jan - 9 Jan 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very good, (2742)
"Clean room and friendly staff, overall good stay "
eesaa saalik
The price is €102
includes taxes & fees
11 Jan - 12 Jan 2026
voco Chicago Downtown - Riverwalk by IHG
voco Chicago Downtown - Riverwalk by IHGRiver North, 12 km from Sleepy Hollow
8.8 out of 10, Excellent, (3462)
"Amazing stay, beautiful view!"
Joshua
The price is €115
includes taxes & fees
29 Dec - 30 Dec
8.6 out of 10, Excellent, (2958)
"Great location and great staff!!"
lynne
The price is €79
includes taxes & fees
14 Jan - 15 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3433)
"Great Hotel!"
Siranush
The price is €130
includes taxes & fees
4 Jan - 5 Jan 2026
9.0 out of 10, Wonderful, (3151)
"Amazing stay very clean and beautiful views "
Deigo
The price is €94
includes taxes & fees
12 Jan - 13 Jan 2026
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.
Where to stay in Sleepy Hollow
Find the best Sleepy Hollow areas for the activities you enjoy most.
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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.
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).
Top Sleepy Hollow Hotel Reviews
Embassy Suites by Hilton Chicago Downtown River North
10/10 Excellent
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Destinations near Chicago
- Hotels in Downtown Chicago
- Hotels in Magnificent Mile
- Hotels in The Loop
- Hotels in River North
- Hotels in Theatre District
- Hotels in Lincoln Park
- Hotels in Streeterville
- Hotels in West Loop
- Hotels in O'Hare
- Hotels in Lakeview
- Hotels in Near North Side
- Hotels in Wrigleyville
- Hotels in West Town
- Hotels in Near South Side
- Hotels in Near West Side
- Hotels in South Loop
- Hotels in Old Town Chicago
- Hotels in Wicker Park
- Hotels in Gold Coast
- Hotels in Fulton Market
More accommodation types in Sleepy Hollow
Hotel Brand
More top Sleepy Hollow Hotels
- River Hotel
- Hyatt Regency Chicago
- citizenM Chicago Downtown
- InterContinental Chicago Magnificent Mile by IHG
- Pendry Chicago
- Sable at Navy Pier Chicago, Curio Collection by Hilton
- Club Quarters Hotel, Central Loop, Chicago
- Crowne Plaza Chicago West Loop by IHG
- Homewood Suites by Hilton Chicago Downtown South Loop
- Swissotel - Chicago
- LondonHouse Chicago, Curio Collection by Hilton
- Hilton Garden Inn Chicago Downtown/Magnificent Mile