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Check prices for these dates

This weekend
15 May - 17 May
Next weekend
22 May - 24 May

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Our top choices for Sleepy Hollow hotels

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Fairfield Inn & Suites Chicago Downtown/River North

Fairfield Inn & Suites Chicago Downtown/River North
3.0 star property
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,242 reviews)
"Nice hotel, very close to river walk."
United States
Luz
The price is SAR 619
SAR 746 total
includes taxes & fees
25 May - 26 May
Fairfield Inn & Suites Chicago Downtown/River North
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, (2,493 reviews)
"Great place to stay "
United States
Mark
The price is SAR 657
SAR 910 total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,446 reviews)
"My favorite place to stay!"
United States
Teresa
The price is SAR 674
SAR 913 total
includes taxes & fees
26 May - 27 May
Palmer House a Hilton Hotel
Room service - dining

The Wade

The Wade
4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very Good, (1,830 reviews)
"We enjoy our stay."
United States
Nuria
The price is SAR 634
SAR 754 total
includes taxes & fees
26 May - 27 May
The Wade
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,153 reviews)
"Great place"
United States
JOSE
The price is SAR 659
SAR 917 total
includes taxes & fees
25 May - 26 May
Fairmont Chicago at Millennium Park
Lobby

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, (10,118 reviews)
"Great location, safe, clean and reasonable price. "
United States
Anthony
The price is SAR 501
SAR 596 total
includes taxes & fees
26 May - 27 May
Congress Plaza Hotel
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, (1,437 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is SAR 615
SAR 731 total
includes taxes & fees
27 May - 28 May
The Chicago Hotel Collection Ambassador Gold Coast
Premium bedding, in-room safe, desk, blackout drapes

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, (2,250 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is SAR 447
SAR 646 total
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.5 km from Sleepy Hollow
7.8 out of 10, Good, (1,411 reviews)
"great place "
United States
Jasar
The price is SAR 427
SAR 508 total
includes taxes & fees
25 May - 26 May
The Chicago Hotel Collection - Magnificent Mile
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,226 reviews)
"Nice place to stay"
United States
Jimmie
The price is SAR 544
SAR 647 total
includes taxes & fees
26 May - 27 May
Aloft by Marriott Chicago Mag Mile
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, (2,989 reviews)
"Great central location, lots to do nearby."
United States
Michael
The price is SAR 334
SAR 464 total
includes taxes & fees
25 May - 26 May
Freehand Chicago
Exterior

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, (3,713 reviews)
"Amazing hotel and staff!"
United States
erin
The price is SAR 735
SAR 984 total
includes taxes & fees
26 May - 27 May
LondonHouse Chicago, Curio Collection by Hilton
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,798 reviews)
"Large rooms, excellent view!"
United States
Liza
The price is SAR 597
SAR 819 total
includes taxes & fees
27 May - 28 May
Hilton Chicago
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, (1,997 reviews)
"Great location and clean room"
United States
Hyacinthe
The price is SAR 520
SAR 618 total
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Chicago Downtown South Loop
Bar (on property)

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,029 reviews)
"Great location right off magnificent mile and close to everything. "
United States
Natalia
The price is SAR 526
SAR 736 total
includes taxes & fees
25 May - 26 May
Warwick Allerton - Chicago
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,144 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is SAR 559
SAR 772 total
includes taxes & fees
25 May - 26 May
Hotel Riu Plaza Chicago
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,323 reviews)
"Wonderful location right on the river. Fitness area wonderful, staff helpful. Would stay again!"
United States
Saleem
The price is SAR 744
SAR 1,016 total
includes taxes & fees
27 May - 28 May
Swissotel - Chicago
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,063 reviews)
"I love this neighborhood , great for shopping and walking. The hotel was super cool with original architecture. "
United States
Susanne
The price is SAR 522
SAR 731 total
includes taxes & fees
25 May - 26 May
Staypineapple, An Iconic Hotel, The Loop
2 bars/lounges

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, (1,623 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is SAR 841
SAR 1,134 total
includes taxes & fees
26 May - 27 May
Sheraton Grand Chicago Riverwalk
In-room safe, iron/ironing board, free WiFi, bed sheets

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,400 reviews)
"Nice location nestled I'm the middle of it all. Great stay the staff was communicative."
United States
Erik
The price is SAR 687
SAR 923 total
includes taxes & fees
27 May - 28 May
Sports Illustrated Resorts Chicago
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

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue 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.

Panoramic view of Lincoln Park and the Chicago skyline.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Top Sleepy Hollow Hotel Reviews

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent
"Clean room, helpful staff. "
James 3-night trip
Posted 1 hour ago
DoubleTree by Hilton Chicago - Magnificent Mile

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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, Jedlica Performing Arts Center, and Balzekas Museum of Lithuanian Culture are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Wintrust Sports Complex and Firehouse Community Arts Center of Chicago are also worth a stop.