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

3

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

￥31,223 total

includes taxes & fees

Mar 24 - Mar 25

Fairmont Chicago at Millennium Park

The Loop, 12.9 km from Sleepy Hollow

Kamilah

￥36,482 total

includes taxes & fees

Mar 24 - Mar 25

Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Brisa

￥25,289 total

includes taxes & fees

Mar 4 - Mar 5

Hilton Chicago

The Loop, 11.7 km from Sleepy Hollow

Andrea

￥28,685 total

includes taxes & fees

Apr 1 - Apr 2

Congress Plaza Hotel

The Loop, 11.9 km from Sleepy Hollow

Jennifer

￥29,742 total

includes taxes & fees

Mar 21 - Mar 22

The Wade

Streeterville, 13.8 km from Sleepy Hollow

Danielle

￥20,122 total

includes taxes & fees

Mar 22 - Mar 23

Aloft Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Pablo

￥16,984 total

includes taxes & fees

Mar 4 - Mar 5

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 12.2 km from Sleepy Hollow

Lori

￥28,936 total

includes taxes & fees

Mar 19 - Mar 20

Swissotel - Chicago

13 km from Sleepy Hollow

Jon

￥27,775 total

includes taxes & fees

Mar 31 - Apr 1

Arlo Chicago

Theatre District, 12.5 km from Sleepy Hollow

Jennifer

￥26,126 total

includes taxes & fees

Mar 25 - Mar 26

The Blackstone, Autograph Collection

The Loop, 11.8 km from Sleepy Hollow

Yu Ching Dexter

￥30,394 total

includes taxes & fees

Mar 5 - Mar 6

Le Méridien Essex Chicago

The Loop, 11.6 km from Sleepy Hollow

Veronica

￥20,132 total

includes taxes & fees

Mar 4 - Mar 5

Hilton Garden Inn Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Quayshaun

￥21,799 total

includes taxes & fees

Mar 18 - Mar 19

Palmer House a Hilton Hotel

Theatre District, 12.1 km from Sleepy Hollow

Melani

￥28,153 total

includes taxes & fees

Apr 1 - Apr 2

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

L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Fernando

￥25,076 total

includes taxes & fees

Mar 31 - Apr 1

Hyatt Centric The Loop Chicago

Theatre District, 11.8 km from Sleepy Hollow

Stephanie

￥22,832 total

includes taxes & fees

Mar 6 - Mar 7

Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Tiffany

￥36,002 total

includes taxes & fees

Apr 1 - Apr 2

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 13.9 km from Sleepy Hollow

Sheila

￥19,148 total

includes taxes & fees

Mar 15 - Mar 16

Eurostars Magnificent Mile

River North, 13 km from Sleepy Hollow

Kylee

￥23,631 total

includes taxes & fees

Mar 4 - Mar 5

River Hotel

The Loop, 12.7 km from Sleepy Hollow

Ian

￥17,105 total

includes taxes & fees

Mar 5 - Mar 6

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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

Aloft Chicago Mag Mile

10/10 Excellent

"This was a quick getaway, very clean and spacious room. Ideal location next to everything Mag Mile, Navy Pier, Shopping, Art Institute. Etc."

The Wade

10/10 Excellent

"My stay at The Wade overall was pretty good. I booked here because it has a pool, and I thought I would have a nice view (city view). The view wasn’t available, I was on the 27th floor and only had a view of the roof of other buildings, and other apartments. I kept the window covered for the most part. The pool was unkept in my opinion, I didn’t feel comfortable with the dirt ring on the white tile that surrounded the pool, and the water looked and felt pretty grimy, I felt it needed to be serviced. Though my main attractions to this location were not fulfilled it was very quiet on my floor, the cleaning crew were very polite and generous, and the valet was very friendly and always gave me great service despite it being very busy over the course of my stay. "

Find hotels in Sleepy Hollow, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Our top choices for Sleepy Hollow hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Fairmont Chicago at Millennium Park

Hotel Riu Plaza Chicago

Hilton Chicago

Congress Plaza Hotel

The Wade

Aloft Chicago Mag Mile

Staypineapple, An Iconic Hotel, The Loop

Swissotel - Chicago

Arlo Chicago

The Blackstone, Autograph Collection

Le Méridien Essex Chicago

Hilton Garden Inn Chicago Downtown South Loop

Palmer House a Hilton Hotel

L7 Chicago by LOTTE

Hyatt Centric The Loop Chicago

Hyatt Regency Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Eurostars Magnificent Mile

River Hotel

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

O'Hare

Top Sleepy Hollow Hotel Reviews

Aloft Chicago Mag Mile

Frequently asked questions

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