Find hotels in Sleepy Hollow, Chicago from ₩131,046

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Dec 10 - Dec 11
Tomorrow
Dec 11 - Dec 12
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

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Our top choices for Sleepy Hollow hotels

Terrace/patio
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2179)
"Nice Hotel"
United States
Alan
The price is ₩131,285
₩154,115 total
includes taxes & fees
Dec 22 - Dec 23
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3136)
"Amazing and will be staying again!"
United States
Angie
The price is ₩137,483
₩161,391 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Eurostars Magnificent Mile
Reception
River Hotel

River Hotel

4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (4842)
"Location of the Hotel is very nice and the hotel is very clean."
United States
Khaing
The price is ₩119,970
₩140,835 total
includes taxes & fees
Dec 23 - Dec 24
River Hotel
Exterior
Hilton Chicago

Hilton Chicago

4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.4 out of 10, Very Good, (2364)
"We had a great stay and will be back again."
United States
Amber
The price is ₩167,418
₩239,641 total
includes taxes & fees
Dec 22 - Dec 23
Hilton Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
Streeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2267)
"Smooth check in and beautiful hotel"
United States
Monique
The price is ₩131,408
₩204,322 total
includes taxes & fees
Dec 16 - Dec 17
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (2947)
"Great location and great staff!!"
United States
lynne
The price is ₩113,101
₩132,770 total
includes taxes & fees
Dec 11 - Dec 12
Aloft Chicago Mag Mile
American cuisine
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 star property
10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1748)
"Good experience would revisit for sure "
United States
james
The price is ₩125,704
₩147,563 total
includes taxes & fees
Dec 14 - Dec 15
Crowne Plaza Chicago West Loop by IHG
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3457)
"Great place to stay "
United States
RaShawna
The price is ₩155,374
₩182,392 total
includes taxes & fees
Dec 17 - Dec 18
Hilton Chicago/Magnificent Mile Suites
Property amenity
citizenM Chicago Downtown

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4107)
"Great stay"
United States
Ericka
The price is ₩157,166
₩184,499 total
includes taxes & fees
Dec 22 - Dec 23
citizenM Chicago Downtown
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
West Loop, 10.8 km from Sleepy Hollow
8.4 out of 10, Very Good, (1004)
"Amazing staff clean and secure hotel "
United States
Aniyah
The price is ₩148,492
₩191,957 total
includes taxes & fees
Dec 25 - Dec 26
Holiday Inn & Suites Chicago - Downtown by IHG
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
River North, 12.9 km from Sleepy Hollow
8.4 out of 10, Very Good, (4239)
"Clean room, very friendly staff and great location "
United States
Marcia
The price is ₩120,558
₩141,524 total
includes taxes & fees
Dec 18 - Dec 19
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2109)
"Great hotel. Very affordable for such a perfect location."
United States
Nicholas
Silversmith Hotel Chicago Downtown
Rooftop terrace
Best Western River North Hotel

Best Western River North Hotel

2.5 star property
River North, 12.6 km from Sleepy Hollow
7.8 out of 10, Good, (1021)
"Loved it will be back. "
United States
Antonio
The price is ₩126,256
₩148,211 total
includes taxes & fees
Dec 28 - Dec 29
Best Western River North Hotel
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
River North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very Good, (369)
"Good place, good location, friendly staff and a great bar! "
United States
Georgi
The price is ₩86,736
₩101,818 total
includes taxes & fees
Jan 5 - Jan 6, 2026
FOUND Hotel Chicago River North
Banquet hall
Congress Plaza Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (9652)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is ₩129,591
₩152,128 total
includes taxes & fees
Dec 11 - Dec 12
Congress Plaza Hotel
Cocktail bar
Freehand Chicago

Freehand Chicago

4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (2634)
"The room was spotless and the staff where great!"
United States
Maria
The price is ₩87,860
₩129,026 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Freehand Chicago
Front of property
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2956)
"Excellent stay great location and great rooms"
United States
Joseph
The price is ₩138,037
₩203,433 total
includes taxes & fees
Dec 17 - Dec 18
Hotel Riu Plaza Chicago
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 star property
Streeterville, 13.5 km from Sleepy Hollow
8.2 out of 10, Very Good, (3785)
"Comfortable Room, great location and Excellent Staff. "
United States
Charles
The price is ₩112,437
₩131,987 total
includes taxes & fees
Dec 22 - Dec 23
The Whitehall Hotel, BW Premier Collection
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1751)
"Clean and staff was courteous. "
United States
HANNAH
The price is ₩104,680
₩122,867 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hilton Garden Inn Chicago Downtown South Loop
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 12.1 km from Sleepy Hollow
8.4 out of 10, Very Good, (2127)
"Loved and enjoyed our stay"
United States
Luis
The price is ₩162,601
₩227,599 total
includes taxes & fees
Dec 22 - Dec 23
Palmer House a Hilton Hotel
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.
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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most.
Downtown Chicago showing a city

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 - River North

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.

The Loop - Downtown which includes a river or creek

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.

River North showing railway items, street scenes and a city

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.

Chicago showing rides

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 the city at Washington Station or Monroe Station (Blue Line).

Top Sleepy Hollow Hotel Reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

10/10 Excellent
"This room was definitely everything plus more than I expected. Great for a couples night or even in solo trip."
DeYanna 1-night trip
Posted 4 hours ago
citizenM Chicago Downtown

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Frequently asked questions

What's it like in Sleepy Hollow?
Sleepy Hollow is a neighborhood that travelers like for its restaurants.
If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?
Yes! The majority of hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals available in Sleepy Hollow.
Where can I learn more about changing or cancelling my trip to Sleepy Hollow?
For more information about picking new dates or cancelling your trip to Sleepy Hollow, click here.
What can I see and do in this Chicago neighborhood?
Hawthorne Works Museum, Balzekas Museum of Lithuanian Culture, and Wintrust Sports Complex are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.