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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Dates

March 2026

April 2026

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Our top choices for Sleepy Hollow hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 14.4 km from Sleepy Hollow

Blake

￥30,604 total

includes taxes & fees

Mar 24 - Mar 25

Swissotel - Chicago

13 km from Sleepy Hollow

Jon

￥27,598 total

includes taxes & fees

Mar 24 - Mar 25

The Wade

Streeterville, 13.8 km from Sleepy Hollow

Danielle

￥18,019 total

includes taxes & fees

Mar 1 - Mar 2

Palmer House a Hilton Hotel

Theatre District, 12.1 km from Sleepy Hollow

Melani

￥31,339 total

includes taxes & fees

Mar 6 - Mar 7

Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Tiffany

￥40,591 total

includes taxes & fees

Mar 24 - Mar 25

Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Brisa

￥22,398 total

includes taxes & fees

Mar 4 - Mar 5

Congress Plaza Hotel

The Loop, 11.9 km from Sleepy Hollow

Jennifer

￥17,611 total

includes taxes & fees

Mar 23 - Mar 24

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 13.9 km from Sleepy Hollow

Sheila

￥19,450 total

includes taxes & fees

Feb 24 - Feb 25

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 12.2 km from Sleepy Hollow

Lori

￥26,655 total

includes taxes & fees

Mar 1 - Mar 2

Aloft Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Pablo

￥15,654 total

includes taxes & fees

Feb 24 - Feb 25

2 restaurants, breakfast, lunch, dinner served; American cuisine

LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.7 km from Sleepy Hollow

Osama

￥35,671 total

includes taxes & fees

Mar 2 - Mar 3

The Blackstone, Autograph Collection

The Loop, 11.8 km from Sleepy Hollow

Yu Ching Dexter

￥29,964 total

includes taxes & fees

Feb 26 - Feb 27

55-inch LCD TV with cable channels, TV, pay movies

L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Fernando

￥29,324 total

includes taxes & fees

Feb 26 - Feb 27

Hilton Chicago

The Loop, 11.7 km from Sleepy Hollow

Andrea

￥29,774 total

includes taxes & fees

Mar 5 - Mar 6

Pendry Chicago

Theatre District, 12.7 km from Sleepy Hollow

Marcelo

￥39,131 total

includes taxes & fees

Mar 15 - Mar 16

Hyatt Centric The Loop Chicago

Theatre District, 11.8 km from Sleepy Hollow

Stephanie

￥21,000 total

includes taxes & fees

Feb 27 - Feb 28

Le Méridien Essex Chicago

The Loop, 11.6 km from Sleepy Hollow

Veronica

￥19,504 total

includes taxes & fees

Mar 16 - Mar 17

Studio, 2 Double Beds | Bathroom | Shower, free toiletries, hair dryer, towels

Sports Illustrated Resorts Chicago

Theatre District, 12.5 km from Sleepy Hollow

Daisy

￥32,726 total

includes taxes & fees

Feb 26 - Feb 27

Radisson Blu Aqua Hotel Chicago

12.9 km from Sleepy Hollow

Michael

￥34,947 total

includes taxes & fees

Mar 11 - Mar 12

Silversmith Hotel Chicago Downtown

Theatre District, 12.2 km from Sleepy Hollow

Corey

￥25,569 total

includes taxes & fees

Mar 22 - Mar 23

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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

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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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.

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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.

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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.

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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.

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Top Sleepy Hollow Hotel Reviews

Hilton Chicago

10/10 Excellent

"The check in process was smooth. Paul provided excellent customer service. The room had a great view of the lake. Everyone we interacted with was very friendly."