Find hotels in Sleepy Hollow, Chicago from ¥11,553

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Discover 4,928 Sleepy Hollow hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2179)
"Great stay "
United States
Melinda
The price is ¥14,542
¥17,069 total
includes taxes & fees
Dec 21 - Dec 22
DoubleTree by Hilton Chicago - Magnificent Mile

River Hotel

4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (4865)
"Front desk is amazing, rooms are clean and great location"
United States
Glen
The price is ¥14,243
¥16,719 total
includes taxes & fees
Dec 7 - Dec 8
River Hotel

Eurostars Magnificent Mile

4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3122)
"Amazing and will be staying again!"
United States
Angie
The price is ¥16,560
¥19,439 total
includes taxes & fees
Dec 4 - Dec 5
Eurostars Magnificent Mile

Hilton Chicago

4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.4 out of 10, Very Good, (2333)
"We had a great stay and will be back again."
United States
Amber
The price is ¥16,455
¥23,884 total
includes taxes & fees
Dec 20 - Dec 21
Hilton Chicago

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)
"Perfect environment and location"
China
YIWEI
The price is ¥14,924
¥22,815 total
includes taxes & fees
Dec 16 - Dec 17
Sable at Navy Pier Chicago, Curio Collection by Hilton

Crowne Plaza Chicago West Loop by IHG

3.5 star property
10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1736)
"The location was great!!"
United States
Yvette
The price is ¥19,787
¥23,229 total
includes taxes & fees
Dec 21 - Dec 22
Crowne Plaza Chicago West Loop by IHG

Aloft Chicago Mag Mile

3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (2959)
"Great location, the staff was friendly and the room was very clean. "
United States
Breanna
The price is ¥13,378
¥15,705 total
includes taxes & fees
Dec 7 - Dec 8
Aloft Chicago Mag Mile

citizenM Chicago Downtown

4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4113)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is ¥16,645
¥19,539 total
includes taxes & fees
Dec 24 - Dec 25
citizenM Chicago Downtown

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3421)
"Great stay!"
United States
Rose
The price is ¥12,958
¥15,211 total
includes taxes & fees
Dec 7 - Dec 8
Hilton Chicago/Magnificent Mile Suites

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, (4230)
"Great location. "
United States
Rodger
The price is ¥12,818
¥15,049 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Silversmith Hotel Chicago Downtown

4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2092)
"Lovely hotel in a great spot!"
United States
Natasha
The price is ¥10,234
¥16,760 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Silversmith Hotel Chicago Downtown

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, (1002)
"Amazing staff clean and secure hotel "
United States
Aniyah
The price is ¥13,565
¥17,792 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn & Suites Chicago - Downtown by IHG

Best Western River North Hotel

2.5 star property
River North, 12.6 km from Sleepy Hollow
7.8 out of 10, Good, (1014)
"Staff was very friendly "
United States
david
The price is ¥13,565
¥15,923 total
includes taxes & fees
Dec 8 - Dec 9
Best Western River North Hotel

Congress Plaza Hotel

3.5 star property
The Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (9696)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is ¥15,086
¥17,710 total
includes taxes & fees
Dec 5 - Dec 6
Congress Plaza Hotel

FOUND Hotel Chicago River North

2.0 star property
River North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very Good, (350)
"love this place definitely coming back !"
United States
Dayanara
The price is ¥9,842
¥11,553 total
includes taxes & fees
Dec 11 - Dec 12
FOUND Hotel Chicago River North

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2899)
"Great service, great breakfast and a nice room "
United States
DeAnna
The price is ¥14,126
¥20,966 total
includes taxes & fees
Dec 8 - Dec 9
Hotel Riu Plaza Chicago

Freehand Chicago

4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (2623)
"Rooms are clean, staff are nice and friendly "
United States
Karen
The price is ¥10,374
¥14,917 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Freehand Chicago

The Whitehall Hotel, BW Premier Collection

3.5 star property
Streeterville, 13.5 km from Sleepy Hollow
8.2 out of 10, Very Good, (3758)
"Great location "
United States
Carlos
The price is ¥12,308
¥14,448 total
includes taxes & fees
Dec 9 - Dec 10
The Whitehall Hotel, BW Premier Collection

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, (1743)
"Staff was courteous, room was clean, convenient location for us. Price was good as well."
United States
Jamie
The price is ¥12,320
¥14,463 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Chicago Downtown South Loop

Palmer House a Hilton Hotel

4.0 star property
Theatre District, 12.1 km from Sleepy Hollow
8.4 out of 10, Very Good, (2123)
"Great place to stay."
United States
Aaron
The price is ¥16,072
¥22,756 total
includes taxes & fees
Dec 28 - Dec 29
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.

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods 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

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

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

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.

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

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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.