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

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Our top choices for Sleepy Hollow hotels

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

1. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Jaclyn

￥34,549 total

includes taxes & fees

Sep 7 - Sep 8

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

￥47,004 total

includes taxes & fees

Sep 7 - Sep 8

A modern interior with a bar area, seating, and decorative wooden panels.

3. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Melissa

￥27,015 total

includes taxes & fees

Sep 7 - Sep 8

4. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

Melanie

￥34,251 total

includes taxes & fees

Sep 7 - Sep 8

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

5. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

LISA

￥37,566 total

includes taxes & fees

Sep 7 - Sep 8

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

6. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Donna

￥32,021 total

includes taxes & fees

Sep 7 - Sep 8

A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

7. Travelodge by Wyndham Downtown Chicago

The Loop, 11.8 km from Sleepy Hollow

Matthew

￥26,616 total

includes taxes & fees

Sep 8 - Sep 9

A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

8. River Hotel

The Loop, 12.7 km from Sleepy Hollow

Timothy

￥29,210 total

includes taxes & fees

Sep 7 - Sep 8

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

9. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Odessia

￥29,033 total

includes taxes & fees

Sep 7 - Sep 8

A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

10. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.6 km from Sleepy Hollow

Shilpa

￥33,792 total

includes taxes & fees

Sep 7 - Sep 8

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

11. Congress Plaza Hotel

The Loop, 11.9 km from Sleepy Hollow

George

￥19,495 total

includes taxes & fees

Sep 7 - Sep 8

A hotel lobby with a bar area, seating, and a large mirror.

12. Hilton Garden Inn Chicago Central Loop

The Loop, 11.4 km from Sleepy Hollow

Theresa

￥35,315 total

includes taxes & fees

Sep 7 - Sep 8

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

13. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Hugo

￥31,764 total

includes taxes & fees

Sep 7 - Sep 8

A spacious lobby with a central coffee table, sofas, and a large mirror.

14. The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 13.9 km from Sleepy Hollow

Laura

￥22,941 total

includes taxes & fees

Sep 8 - Sep 9

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

15. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

susie

￥29,982 total

includes taxes & fees

Sep 7 - Sep 8

An outdoor seating area with sofas and tables, surrounded by greenery and modern buildings in the background.

16. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

11.4 km from Sleepy Hollow

Amber

￥47,024 total

includes taxes & fees

Sep 8 - Sep 9

A breakfast buffet with a variety of fruits, pastries, and beverages on a wooden table, set against a modern room with a white sofa and a wooden accent wall.

17. Holiday Inn & Suites Chicago - Downtown by IHG

West Loop, 10.8 km from Sleepy Hollow

Julenny

￥32,299 total

includes taxes & fees

Sep 7 - Sep 8

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

18. citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

lakadria

￥32,093 total

includes taxes & fees

Sep 8 - Sep 9

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.

19. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Jeff

￥48,776 total

includes taxes & fees

Sep 20 - Sep 21

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

20. Carleton of Oak Park

9.6 km from Sleepy Hollow

Alan

￥16,504 total

includes taxes & fees

Sep 21 - Sep 22

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Where to stay in Sleepy Hollow

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

A busy city street with tall buildings, a bus, and cars.

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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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.

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A historic castle-like building with intricate stonework and a paved walkway.

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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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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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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.

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Top Sleepy Hollow Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"staff were very friendly and helpful"

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"The roof top was a nice change in our Chicago stay. However the staff was kind of rude and not very helpful. They didn’t notify me of the $150 deposit until check in, and when I asked when it would be returned they said it’s up to my bank. Days later my bank is still saying it’s a pending charge on the hotels end. A bit frustrating. The room was nice, not what was shown in the pictures and the city view for the suit was an alley. Don’t think I will be staying there again."

Find hotels in Sleepy Hollow, Chicago

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Our top choices for Sleepy Hollow hotels

1. Crowne Plaza Chicago West Loop by IHG

2. Hyatt House Chicago/West Loop-Fulton Market

3. Best Western Grant Park Hotel

4. Hilton Vacation Club Hotel Blake Chicago

5. Hyatt Place Chicago/Downtown - The Loop

6. Hotel Riu Plaza Chicago

7. Travelodge by Wyndham Downtown Chicago

8. River Hotel

9. Aloft by Marriott Chicago Mag Mile

10. La Quinta Inn & Suites by Wyndham Chicago Downtown

11. Congress Plaza Hotel

12. Hilton Garden Inn Chicago Central Loop

13. Embassy Suites by Hilton Chicago Downtown River North

14. The Chicago Hotel Collection Ambassador Gold Coast

15. Hilton Chicago/Magnificent Mile Suites

16. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

17. Holiday Inn & Suites Chicago - Downtown by IHG

18. citizenM Chicago Downtown

19. L7 Chicago by LOTTE

20. Carleton of Oak Park

Where to stay in Sleepy Hollow

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

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