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Check prices for these dates

Tonight
Jan 17 - Jan 18
Tomorrow
Jan 18 - Jan 19
Next weekend
Jan 23 - Jan 25
In two weeks
Jan 30 - Feb 1

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Our top choices for Sleepy Hollow hotels

Exterior

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, (1,517 reviews)
"Clean room, staff was very nice and it was in a very nice location! "
United States
Mary
The price is ￥8,946
￥15,144 total
includes taxes & fees
Feb 1 - Feb 2
Claridge House Chicago, Tapestry Collection by Hilton
Meeting facility

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, (1,310 reviews)
"Love this hotel, right in the middle of a great area re: restaurants, bars, night scene, etc. "
United States
Yoshio
The price is ￥21,346
￥29,723 total
includes taxes & fees
Jan 30 - Jan 31
Thompson Chicago, by Hyatt
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, (2,318 reviews)
"Great stay!"
United States
Angela
The price is ￥16,666
￥24,949 total
includes taxes & fees
Feb 4 - Feb 5
Sable at Navy Pier Chicago, Curio Collection by Hilton
Serves breakfast, lunch, and dinner

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (870 reviews)
"Great hotel, lots of fun and great location! "
United States
Amber
The price is ￥17,077
￥20,045 total
includes taxes & fees
Jan 25 - Jan 26
Moxy Chicago Downtown
Smart TV

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, (382 reviews)
"The experience of the hotel was amazing"
United States
Lachelle
Level Chicago Fulton Market
2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,002 reviews)
"The Hoxton was such s beautiful place to stay, I loved the convenience of a speakeasy and a restaurant and bar in one spot, not only that it is conveniently located in a area where so many bars and restaurants are in walking distance"
United States
Shavon
The Hoxton Chicago
Terrace/patio

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,003 reviews)
"Room was clean staff wasexcellent breakfast was great"
United States
Jerry
The price is ￥20,616
￥24,200 total
includes taxes & fees
Jan 24 - Jan 25
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Exterior

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,299 reviews)
"Great hotel !"
United States
Dr. Mark
The price is ￥25,402
￥34,462 total
includes taxes & fees
Jan 19 - Jan 20
Sofitel Chicago Magnificent Mile
Exterior

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, (1,016 reviews)
"Room was super clean, staff was friendly and helpful, and the area was a perfect spot in town!"
United States
Zachary
The price is ￥16,800
￥19,721 total
includes taxes & fees
Jan 25 - Jan 26
Springhill Suites by Marriott Chicago Downtown/ River North
City view from property

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, (1,160 reviews)
"The room was comfortable, the breakfast was nice and the staff (in person) were responsive. It's also in a good location. "
Canada
Carol
The price is ￥22,769
￥26,728 total
includes taxes & fees
Jan 24 - Jan 25
Hyatt House Chicago West Loop
Exterior

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, (1,006 reviews)
"Nice hotel and staff. "
United States
Wendy
The price is ￥20,026
￥23,509 total
includes taxes & fees
Jan 24 - Jan 25
Hampton Inn Chicago West Loop Fulton Market Area
Cocktail bar

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, (1,928 reviews)
"Love the location, room, staff, and bar."
United States
Jason
The price is ￥11,540
￥13,548 total
includes taxes & fees
Jan 25 - Jan 26
ACME Hotel Chicago, Outset Collection by Hilton
2 restaurants, breakfast, lunch, dinner served; American cuisine

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, (3,543 reviews)
"Clean accommodations and friendly staff."
United States
usha
The price is ￥21,912
￥25,722 total
includes taxes & fees
Jan 25 - Jan 26
LondonHouse Chicago, Curio Collection by Hilton
Lobby

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2.5 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,001 reviews)
"The room was cozy and breakfast was very good and the staff were very kind and welcoming."
United States
Ibrahim
The price is ￥14,073
￥16,520 total
includes taxes & fees
Jan 22 - Jan 23
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Lunch and dinner served

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, (1,819 reviews)
"Great hotel"
United States
Yavuz
The price is ￥24,350
￥32,695 total
includes taxes & fees
Feb 1 - Feb 2
Radisson Blu Aqua Hotel Chicago
Exterior detail

The Emily Hotel

The Emily Hotel
4.0 star property
11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,296 reviews)
"The room was spotless, the people were accommodating and very nice, and it was a great quiet stay! "
United States
Stephanie
The price is ￥57,070
￥66,995 total
includes taxes & fees
Jan 20 - Jan 21
The Emily Hotel
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, (4,171 reviews)
"Super clean, friendly staff, amazing breakfast, unbeatable location"
United States
Ken
The price is ￥15,322
￥17,987 total
includes taxes & fees
Feb 1 - Feb 2
citizenM Chicago Downtown
Indoor pool

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, (4,327 reviews)
"Amazing staff and perfect location "
United States
Brandi
The price is ￥13,095
￥15,373 total
includes taxes & fees
Feb 1 - Feb 2
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very Good, (1,268 reviews)
"Solid stay in a great part of town"
United States
Michael
The price is ￥18,168
￥21,327 total
includes taxes & fees
Jan 19 - Jan 20
The Chicago Hotel Collection Ambassador Gold Coast
Exterior

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, (2,112 reviews)
"Excellent hotel plus very good location"
Canada
Tomas Colocol
The price is ￥16,041
￥18,833 total
includes taxes & fees
Jan 18 - Jan 19
Holiday Inn Chicago Dwtn - The Mart by IHG
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.

Rosemont

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

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent
"El lugar es espectacular "
Laura 1-night trip
Posted 14 hours ago
Club Quarters Hotel Wacker at Michigan, Chicago

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.

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