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

Top Sleepy Hollow Hotels

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Our top choices for Sleepy Hollow hotels

1. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Hadi

￥46,148 total

includes taxes & fees

Jul 26 - Jul 27

2. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

Kimberly

￥39,195 total

includes taxes & fees

Aug 9 - Aug 10

3. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Bethany

￥34,869 total

includes taxes & fees

Aug 10 - Aug 11

4. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.6 km from Sleepy Hollow

Diana

￥37,302 total

includes taxes & fees

Aug 9 - Aug 10

Suite, 1 Bedroom, Corner | Private kitchen | Coffee/tea maker, full-size fridge, microwave, stovetop

5. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

jayne

￥36,256 total

includes taxes & fees

Aug 10 - Aug 11

6. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Sonyce

￥36,106 total

includes taxes & fees

Aug 9 - Aug 10

7. Hilton Garden Inn Chicago Central Loop

The Loop, 11.4 km from Sleepy Hollow

Malachi

￥39,743 total

includes taxes & fees

Aug 9 - Aug 10

8. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Loop, 11.6 km from Sleepy Hollow

Dean

￥35,371 total

includes taxes & fees

Aug 9 - Aug 10

9. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Jessica

￥44,983 total

includes taxes & fees

Aug 9 - Aug 10

10. Hampton Inn Chicago West Loop Fulton Market Area

11.4 km from Sleepy Hollow

Michele

￥47,539 total

includes taxes & fees

Aug 9 - Aug 10

11. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 13 km from Sleepy Hollow

Amy

￥48,030 total

includes taxes & fees

Aug 9 - Aug 10

12. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Mark

￥32,823 total

includes taxes & fees

Aug 9 - Aug 10

13. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Tammy

￥32,847 total

includes taxes & fees

Aug 11 - Aug 12

Premium bedding, in-room safe, desk, blackout drapes

14. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Zachary

￥41,514 total

includes taxes & fees

Aug 9 - Aug 10

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

11.4 km from Sleepy Hollow

Jihi

￥46,547 total

includes taxes & fees

Aug 16 - Aug 17

16. Travelodge by Wyndham Downtown Chicago

The Loop, 11.8 km from Sleepy Hollow

MARTINA

￥32,493 total

includes taxes & fees

Aug 17 - Aug 18

17. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Michael

￥45,773 total

includes taxes & fees

Aug 9 - Aug 10

18. citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

lakadria

￥39,773 total

includes taxes & fees

Aug 9 - Aug 10

19. Hampton Inn Majestic Chicago Theatre District

Theatre District, 12 km from Sleepy Hollow

Naidy

￥40,676 total

includes taxes & fees

Aug 9 - Aug 10

20. Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Kristen

￥56,767 total

includes taxes & fees

Aug 9 - Aug 10

View all properties

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 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 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 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

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent

"We only stayed one night, but the room was clean. Staff was very helpful."

Hyatt Regency Chicago

10/10 Excellent

"I had a wonderful stay. The location was perfect—right along the river and within walking distance of many of Chicago’s top attractions, restaurants, and shopping. The hotel was clean, modern, and well-maintained. My room was spacious, comfortable, and offered beautiful views of the city. The staff was friendly, professional, and always willing to help. The standard check-in is at 3 pm but when I arrived at 11 am the staff was able to give me a room upon my arrival. My entire stay smooth and enjoyable."

Hotel Riu Plaza Chicago

10/10 Excellent

"Our room on the 26th floor was outstanding!!! We went to breakfast early because the first morning was a zoo with children running around and absent parents. Scrambled eggs are always tricky when made for 100 people but the hot sauce made them edible. Traffic pattern at breakfast was a bit congested with people going in all directions at once."

Find hotels in Sleepy Hollow, Chicago

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Treat yourself

Be picky

Check prices for these dates

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Our top choices for Sleepy Hollow hotels

1. Hyatt House Chicago/West Loop-Fulton Market

2. Hyatt Place Chicago/Downtown - The Loop

3. Crowne Plaza Chicago West Loop by IHG

4. La Quinta Inn & Suites by Wyndham Chicago Downtown

5. Homewood Suites by Hilton Chicago Downtown South Loop

6. Aloft by Marriott Chicago Mag Mile

7. Hilton Garden Inn Chicago Central Loop

8. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

9. Hotel Riu Plaza Chicago

10. Hampton Inn Chicago West Loop Fulton Market Area

11. InterContinental Chicago Magnificent Mile by IHG

12. Hyatt Place Chicago/River North

13. Best Western Grant Park Hotel

14. Courtyard by Marriott Chicago Magnificent Mile

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

16. Travelodge by Wyndham Downtown Chicago

17. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

18. citizenM Chicago Downtown

19. Hampton Inn Majestic Chicago Theatre District

20. Hyatt Regency Chicago

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

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