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?

Douglas Park, Hawthorne Race Course, and Hawthorne Works Museum are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Jedlica Performing Arts Center and Los Globos are also worth a stop.

Top Sleepy Hollow Hotels

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

Tomorrow

This weekend

Next weekend

Our top choices for Sleepy Hollow hotels

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

1. Carleton of Oak Park

9.6 km from Sleepy Hollow

Brad

NT$4,334 total

includes taxes & fees

Oct 12 - Oct 13

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

2. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Joel

NT$9,445 total

includes taxes & fees

Oct 31 - Nov 1

A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

3. Hampton Inn Chicago-O'Hare International Airport

19.4 km from Sleepy Hollow

karen

NT$5,136 total

includes taxes & fees

Oct 30 - Oct 31

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

4. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Sean Robert

NT$9,836 total

includes taxes & fees

Oct 25 - Oct 26

A modern kitchen with a large window, a dining area, and a view of the sea.

5. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Cecilia

NT$7,383 total

includes taxes & fees

Oct 31 - Nov 1

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

6. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.7 km from Sleepy Hollow

Sharee

NT$10,451 total

includes taxes & fees

Oct 25 - Oct 26

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

7. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Eliana

NT$8,400 total

includes taxes & fees

Oct 26 - Oct 27

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

8. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Iminique

NT$8,193 total

includes taxes & fees

Oct 31 - Nov 1

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

9. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

John

NT$11,934 total

includes taxes & fees

Oct 21 - Oct 22

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

10. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Tim

NT$8,123 total

includes taxes & fees

Oct 25 - Oct 26

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

11. Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Mark

NT$10,126 total

includes taxes & fees

Oct 31 - Nov 1

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

12. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Aran

NT$7,065 total

includes taxes & fees

Oct 25 - Oct 26

A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

13. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Emily

NT$9,402 total

includes taxes & fees

Oct 31 - Nov 1

A modern lobby with a geometric light installation, a staircase, and a reception desk.

14. Hampton Inn & Suites Chicago Downtown

River North, 12.7 km from Sleepy Hollow

Catherine

NT$8,624 total

includes taxes & fees

Oct 26 - Oct 27

A modern building with a colorful facade and a red circular seating area.

15. citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

Kimberly

NT$7,783 total

includes taxes & fees

Oct 25 - Oct 26

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

16. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Alan

NT$6,552 total

includes taxes & fees

Oct 25 - Oct 26

A multi-story hotel with a prominent sign reading "Crowne Plaza."

17. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Phillip

NT$7,130 total

includes taxes & fees

Oct 25 - Oct 26

A modern hotel with a glass facade, multiple floors, and a visible entrance.

18. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

Lauren

NT$8,010 total

includes taxes & fees

Oct 25 - Oct 26

An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.

19. The Emily Hotel

11.1 km from Sleepy Hollow

Leslie

NT$8,732 total

includes taxes & fees

Oct 4 - Oct 5

A swimming pool with lounge chairs and umbrellas, surrounded by high-rise buildings.

20. Hilton Grand Vacations Club Chicago Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Shaniyah

NT$10,503 total

includes taxes & fees

Oct 26 - Oct 27

View all properties

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most.

A cityscape with tall skyscrapers and a historic tower.

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.

See properties

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

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.

See properties

A river with yellow boats, a bridge, and tall buildings.

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.

See properties

A large, historic building with a central tower and multiple windows, located near a body of water.

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.

See properties

A river with a city skyline in the background, surrounded by green trees and grass.

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.

See properties

Top Sleepy Hollow Hotel Reviews

Hilton Chicago

8/10 Good

"It was my first time in Chicago. Stay was ok. But breakfast was not included."

L7 Chicago by LOTTE

8/10 Good

"Nice bed in our king room. Location was perfect for us for all we had planned and coming in the CTA from midway . Disappointed no bar just the one next door at the restaurant that wasn’t open late at all . We flew in very early in morning hoped to get into a room early even if we had to pay extra but the check in person was no help at all in regards to check in early or any of our questions . Our family came in the next morning same time and this time a different check in person actually offered them to check in early ! We had nowhere to go so we walked a lot of the city waiting to check in . I think we walked 13 miles . Our room ,once we got it ,was nice tho we didn’t get the city view just the view across to a building and parking . Location was definitely the highlight of this hotel ."

Find hotels in Sleepy Hollow, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sleepy Hollow hotels

1. Carleton of Oak Park

2. Hyatt House Chicago/West Loop-Fulton Market

3. Hampton Inn Chicago-O'Hare International Airport

4. Hotel Riu Plaza Chicago

5. Homewood Suites by Hilton Chicago Downtown South Loop

6. LondonHouse Chicago, Curio Collection by Hilton

7. Embassy Suites by Hilton Chicago Downtown River North

8. Hyatt Place Chicago/River North

9. Hilton Vacation Club Hotel Blake Chicago

10. Courtyard by Marriott Chicago Magnificent Mile

11. Hyatt Regency Chicago

12. Hilton Garden Inn Chicago Downtown South Loop

13. L7 Chicago by LOTTE

14. Hampton Inn & Suites Chicago Downtown

15. citizenM Chicago Downtown

16. Hilton Chicago/Magnificent Mile Suites

17. Crowne Plaza Chicago West Loop by IHG

18. Hyatt Place Chicago/Downtown - The Loop

19. The Emily Hotel

20. Hilton Grand Vacations Club Chicago Magnificent Mile

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Hilton Chicago

Frequently asked questions

Explore a world of travel with Expedia