Find hotels in Sleepy Hollow, Chicago from AED 315

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
20 Jan - 21 Jan
Tomorrow
21 Jan - 22 Jan
This weekend
23 Jan - 25 Jan
Next weekend
30 Jan - 1 Feb

Filter by

Guest rating
Guest rating
Star rating

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 AED 208
AED 352 total
includes taxes & fees
1 Feb - 2 Feb
Claridge House Chicago, Tapestry Collection by Hilton
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, (2,329 reviews)
"Great stay"
United States
Blake
The price is AED 374
AED 564 total
includes taxes & fees
17 Feb - 18 Feb
Sable at Navy Pier Chicago, Curio 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, (1,312 reviews)
"Love this hotel, right in the middle of a great area re: restaurants, bars, night scene, etc. "
United States
Yoshio
The price is AED 533
AED 734 total
includes taxes & fees
12 Feb - 13 Feb
Thompson Chicago, by Hyatt
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, (872 reviews)
"Great hotel, lots of fun and great location! "
United States
Amber
The price is AED 380
AED 446 total
includes taxes & fees
25 Jan - 26 Jan
Moxy Chicago Downtown
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, (4,185 reviews)
"Super clean, friendly staff, amazing breakfast, unbeatable location"
United States
Ken
The price is AED 378
AED 444 total
includes taxes & fees
26 Jan - 27 Jan
citizenM Chicago Downtown
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, (1,271 reviews)
"Solid stay in a great part of town"
United States
Michael
The price is AED 440
AED 517 total
includes taxes & fees
21 Jan - 22 Jan
The Chicago Hotel Collection Ambassador Gold Coast
Signature Suite, 1 Bedroom, 1 King Bed, 1 Sofabed | Premium bedding, in-room safe, individually decorated

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,306 reviews)
"Great hotel !"
United States
Dr. Mark
The price is AED 590
AED 801 total
includes taxes & fees
21 Jan - 22 Jan
Sofitel Chicago Magnificent Mile
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, (386 reviews)
"The experience of the hotel was amazing"
United States
Lachelle
Level Chicago Fulton Market
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, (4,340 reviews)
"All things about this hotel was good from the location to the staff"
United States
Cisco
The price is AED 313
AED 368 total
includes taxes & fees
1 Feb - 2 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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, (1,006 reviews)
"Amazing, I loved my stay"
United States
Valerie
The Hoxton Chicago
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, (1,025 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 AED 422
AED 496 total
includes taxes & fees
25 Jan - 26 Jan
Springhill Suites by Marriott Chicago Downtown/ River North
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, (3,573 reviews)
"Clean accommodations and friendly staff."
United States
usha
The price is AED 509
AED 598 total
includes taxes & fees
8 Feb - 9 Feb
LondonHouse Chicago, Curio Collection by Hilton
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, (1,832 reviews)
"Great hotel"
United States
Yavuz
The price is AED 566
AED 760 total
includes taxes & fees
2 Feb - 3 Feb
Radisson Blu Aqua Hotel Chicago
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, (1,934 reviews)
"Love the location, room, staff, and bar."
United States
Jason
The price is AED 268
AED 315 total
includes taxes & fees
26 Jan - 27 Jan
ACME Hotel Chicago, Outset Collection by Hilton
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, (1,008 reviews)
"Nice hotel and staff. "
United States
Wendy
The price is AED 465
AED 546 total
includes taxes & fees
30 Jan - 31 Jan
Hampton Inn Chicago West Loop Fulton Market Area
Bar (on property)

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, (3,903 reviews)
"Location, breakfast was good, room was nice. "
United States
Traci
The price is AED 281
AED 330 total
includes taxes & fees
25 Jan - 26 Jan
The Whitehall Hotel, BW Premier Collection
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, (1,005 reviews)
"Room was clean staff wasexcellent breakfast was great"
United States
Jerry
The price is AED 479
AED 562 total
includes taxes & fees
30 Jan - 31 Jan
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
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, (1,005 reviews)
"The room was cozy and breakfast was very good and the staff were very kind and welcoming."
United States
Ibrahim
The price is AED 327
AED 384 total
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
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, (2,257 reviews)
"Great staff, easy check in."
United States
Zachary
The price is AED 313
AED 368 total
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Chicago - Magnificent Mile
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, (1,168 reviews)
"Only stayed one night but really enjoyed our stay. "
United States
Michael
The price is AED 529
AED 621 total
includes taxes & fees
29 Jan - 30 Jan
Hyatt House Chicago West Loop
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.
View all properties

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

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 - 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

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"Rooms were clean, atmosphere fun-music, seating, felt like home great for families, and social options too. Great ambiance, food snacks appeared to be on an honor ststem- snacks and food available access - easily able to grab and go just add items through QR code or guest services. Great response from staff. One of 2 elevators down. So only one available elevator and service elevator. There was frequently a line since 19 floors or more building. Didn’t get to try the pool. But it was perfectly located walking distance from most attractions. Great food across the street and less than one block away. Nice staff. Highly reccomended return for sure"
Alicia 3-night trip
Posted 10 hours ago
Aloft Chicago Mag Mile

Explore a world of travel with Expedia

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.