Find hotels in Sleepy Hollow, Chicago from AED 350

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Our top choices for Sleepy Hollow hotels

Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,527 reviews)
"Great location, friendly staff and nice room"
United States
Srinivasa
The price is AED 208
AED 352 total
includes taxes & fees
22 Feb - 23 Feb
Claridge House Chicago, Tapestry Collection by Hilton

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Gold Coast, 13.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,316 reviews)
"great stay"
United States
Loan
The price is AED 496
AED 690 total
includes taxes & fees
1 Mar - 2 Mar
Thompson Chicago, by Hyatt

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, (2,371 reviews)
"Great stay"
United States
Blake
The price is AED 450
AED 653 total
includes taxes & fees
22 Feb - 23 Feb
Sable at Navy Pier Chicago, Curio Collection by Hilton

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (888 reviews)
"Clean, friendly staff, and excellent location "
United States
Paulina
The price is AED 397
AED 466 total
includes taxes & fees
22 Feb - 23 Feb
Moxy Chicago Downtown

Level Chicago Fulton Market

Level Chicago Fulton Market
4.0 star property
West Loop, 11.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (402 reviews)
"The hotel in it’s entirety was better than advertised "
United States
Eric
Level Chicago Fulton Market

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,002 reviews)
"Amazing, I loved my stay"
United States
Valerie
The Hoxton Chicago

Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,049 reviews)
"Great hotel, good food and great service ! "
United States
Fernando
The price is AED 422
AED 496 total
includes taxes & fees
22 Feb - 23 Feb
Springhill Suites by Marriott Chicago Downtown/ River North

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice hotel and staff. "
United States
Wendy
The price is AED 465
AED 546 total
includes taxes & fees
21 Feb - 22 Feb
Hampton Inn Chicago West Loop Fulton Market Area

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
10.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,188 reviews)
"Great location, friendly staff, spacious room"
United States
Mary
The price is AED 529
AED 621 total
includes taxes & fees
22 Feb - 23 Feb
Hyatt House Chicago West Loop

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,315 reviews)
"Staff was friendly and helpful! Great stay!"
United States
Kristin
The price is AED 653
AED 874 total
includes taxes & fees
16 Feb - 17 Feb
Sofitel Chicago Magnificent Mile

ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 12.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,954 reviews)
"Very convenient place to stay friendly and helpful staff."
United States
Rick
The price is AED 298
AED 350 total
includes taxes & fees
22 Feb - 23 Feb
ACME Hotel Chicago, Outset Collection by Hilton

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,855 reviews)
"Room was very nice, views were fantastic and the restaurant was excellent "
United States
Michael
The price is AED 625
AED 829 total
includes taxes & fees
22 Feb - 23 Feb
Radisson Blu Aqua Hotel Chicago

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,604 reviews)
"Staff was friendly and loved the decor at this hotel…will definitely be staying again"
Canada
Osama
The price is AED 599
AED 704 total
includes taxes & fees
22 Feb - 23 Feb
LondonHouse Chicago, Curio Collection by Hilton

The Emily Hotel

The Emily Hotel
4.0 star property
11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,299 reviews)
"Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again. "
United States
Mary
The price is AED 1,068
AED 1,253 total
includes taxes & fees
21 Feb - 22 Feb
The Emily Hotel

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,593 reviews)
"We had a great stay! Everything was great!"
United States
Megan
The price is AED 590
AED 822 total
includes taxes & fees
22 Feb - 23 Feb
Sheraton Grand Chicago Riverwalk

Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
4.0 star property
The Loop, 11.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,480 reviews)
"Great place to stay…near to many nice places to visit."
United States
Jorge
The price is AED 509
AED 598 total
includes taxes & fees
21 Feb - 22 Feb
Canopy by Hilton Chicago Central Loop

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
8.6 out of 10, Excellent, (4,363 reviews)
"Great staff, great room, and close to everything "
United States
George
The price is AED 301
AED 354 total
includes taxes & fees
22 Feb - 23 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
River North, 11.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,171 reviews)
"Great location"
United States
Adam
The price is AED 426
AED 500 total
includes taxes & fees
1 Mar - 2 Mar
Holiday Inn Chicago Dwtn - The Mart by IHG

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,214 reviews)
"Friendly staff, cozy room, good location. "
United States
Andrew
The price is AED 393
AED 461 total
includes taxes & fees
22 Feb - 23 Feb
citizenM Chicago Downtown

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 13.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,696 reviews)
"Great place to stay "
United States
Juliet
The price is AED 555
AED 760 total
includes taxes & fees
16 Feb - 17 Feb
Omni Chicago 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

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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.

O'Hare

Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.

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.