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Check prices for these dates

Tonight
3 May - 4 May
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4 May - 5 May
Next weekend
8 May - 10 May
In two weeks
15 May - 17 May

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Our top choices for Sleepy Hollow hotels

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, (2,486 reviews)
"Great place to stay "
United States
Mark
The price is SAR 689
SAR 948 total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier 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, (2,773 reviews)
"Clean room and great location "
United States
Diana
The price is SAR 596
SAR 819 total
includes taxes & fees
25 May - 26 May
Hilton 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, (4,039 reviews)
"It was great property, amazing location and the breakfast was fantastic. "
United States
Nichole
The price is SAR 505
SAR 706 total
includes taxes & fees
27 May - 28 May
Hotel Riu Plaza 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, (1,980 reviews)
"Had a great stay-5 stars of 5"
United States
donald
The price is SAR 491
SAR 584 total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop
55-inch LCD TV with cable channels, TV, pay movies

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (4,004 reviews)
"Clean hotel great restaurant "
United States
ELIZABETH
The price is SAR 571
SAR 678 total
includes taxes & fees
10 May - 11 May
L7 Chicago by LOTTE
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, (10,144 reviews)
"Great stay"
United States
Matthew
The price is SAR 470
SAR 559 total
includes taxes & fees
8 May - 9 May
Congress Plaza Hotel
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, (2,944 reviews)
"Great stay"
United States
Agnes Nmabila
The price is SAR 350
SAR 483 total
includes taxes & fees
25 May - 26 May
Freehand Chicago
Lobby

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, (2,244 reviews)
"This was a great hotel. The staff and accommodations were terrific. I really enjoyed my stay "
United States
Alex
The price is SAR 447
SAR 646 total
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
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, (1,056 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is SAR 521
SAR 730 total
includes taxes & fees
10 May - 11 May
Staypineapple, An Iconic Hotel, The Loop
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,297 reviews)
"Very good, would stay here again!"
United States
Lorena
The price is SAR 743
SAR 1,016 total
includes taxes & fees
27 May - 28 May
Swissotel - Chicago
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, (3,685 reviews)
"Loved staying at this hotel"
United States
Kimberly Marie
The price is SAR 694
SAR 935 total
includes taxes & fees
10 May - 11 May
LondonHouse 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, (2,428 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is SAR 714
SAR 961 total
includes taxes & fees
26 May - 27 May
Palmer House a Hilton Hotel
Exterior detail

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very Good, (582 reviews)
"Great location great staff great hotel!"
United States
Refak
The price is SAR 334
SAR 392 total
includes taxes & fees
25 May - 26 May
FOUND Hotel Chicago River North
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 11.8 km from Sleepy Hollow
7.4 out of 10, Good, (2,575 reviews)
"Perfect location for a good price that aside, mid hotel "
United States
Nicolas Esteban
The price is SAR 395
SAR 470 total
includes taxes & fees
27 May - 28 May
Travelodge by Wyndham Downtown Chicago
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,158 reviews)
"Excellent location, very clean room and friendly staff"
United States
Alejandra
The price is SAR 596
SAR 709 total
includes taxes & fees
26 May - 27 May
River Hotel
Restaurant

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,689 reviews)
"Great location, right across the street from the park."
United States
Jamison
The price is SAR 435
SAR 518 total
includes taxes & fees
27 May - 28 May
Best Western Grant Park Hotel
Nightclub

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,106 reviews)
"Clean rooms and very good location. "
Canada
Rudra
The price is SAR 349
SAR 414 total
includes taxes & fees
25 May - 26 May
Central Loop Hotel
Lobby

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 11.6 km from Sleepy Hollow
8.4 out of 10, Very Good, (1,009 reviews)
"A fantastic hotel for solo travelers - perfect area, close to museums and restaurants, great bar"
United States
Michelle Renee
The price is SAR 559
SAR 664 total
includes taxes & fees
10 May - 11 May
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
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, (1,365 reviews)
"It was in a great location near everything. "
United States
Dwight Demond
The price is SAR 455
SAR 541 total
includes taxes & fees
10 May - 11 May
The Chicago Hotel Collection - Magnificent Mile
Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,220 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is SAR 559
SAR 664 total
includes taxes & fees
10 May - 11 May
Aloft Chicago Mag Mile
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.

USA, Illinois, Chicago, Lincoln Park lagoon

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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Room was very clean, very comfortable bed and pillow, great location, guy at front desk was very nice and friendly, would definitely stay there again"
Sharon 2-night trip
Posted 2 hours ago
The Chicago Hotel Collection - 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.