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. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.6 km from Sleepy Hollow

Paige

￥34,713 total

includes taxes & fees

Aug 9 - Aug 10

2. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Hadi

￥46,115 total

includes taxes & fees

Aug 16 - Aug 17

3. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

Kimberly

￥38,052 total

includes taxes & fees

Aug 16 - Aug 17

4. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Evelyn

￥38,559 total

includes taxes & fees

Aug 20 - Aug 21

5. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Jasmin

￥33,742 total

includes taxes & fees

Aug 16 - Aug 17

6. Hilton Garden Inn Chicago Central Loop

The Loop, 11.4 km from Sleepy Hollow

Dawn

￥39,676 total

includes taxes & fees

Aug 16 - Aug 17

7. River Hotel

The Loop, 12.7 km from Sleepy Hollow

Yousef

￥26,643 total

includes taxes & fees

Aug 9 - Aug 10

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

8. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Julie Ann

￥35,242 total

includes taxes & fees

Aug 9 - Aug 10

9. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

The Loop, 11.6 km from Sleepy Hollow

Aleace

￥31,340 total

includes taxes & fees

Aug 30 - Aug 31

10. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Cicely

￥41,702 total

includes taxes & fees

Aug 31 - Sep 1

11. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 13 km from Sleepy Hollow

Jose

￥53,131 total

includes taxes & fees

Sep 2 - Sep 3

12. Travelodge by Wyndham Downtown Chicago

The Loop, 11.8 km from Sleepy Hollow

Adam

￥21,155 total

includes taxes & fees

Aug 30 - Aug 31

13. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Michelle

￥31,867 total

includes taxes & fees

Aug 31 - Sep 1

14. Swissotel - Chicago

13 km from Sleepy Hollow

Isaac

￥54,166 total

includes taxes & fees

Aug 9 - Aug 10

Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

15. Holiday Inn & Suites Chicago - Downtown by IHG

West Loop, 10.8 km from Sleepy Hollow

Chimere

￥36,400 total

includes taxes & fees

Aug 30 - Aug 31

16. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Adit

￥26,827 total

includes taxes & fees

Aug 30 - Aug 31

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

17. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

jayne

￥30,114 total

includes taxes & fees

Aug 31 - Sep 1

18. Hampton Inn Chicago West Loop Fulton Market Area

11.4 km from Sleepy Hollow

Michele

￥39,658 total

includes taxes & fees

Aug 16 - Aug 17

19. Omni Chicago Hotel

Streeterville, 13.2 km from Sleepy Hollow

Melissa

￥47,052 total

includes taxes & fees

Aug 10 - Aug 11

20. The Emily Hotel

11.1 km from Sleepy Hollow

Heather

￥46,406 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 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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The Chicago Theatre with illuminated marquee and a wet street reflecting lights.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

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Top Sleepy Hollow Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Always love staying at the ambassador! So much old charm but modern amenities and gorgeous design. Located in a lovely quiet neighborhood north of the loop with lots of walkable cafes and restaurants."

Holiday Inn & Suites Chicago - Downtown by IHG

10/10 Excellent

"Front desk staff Every front desk person was friendly and helpful Room Spacious and Recently updated Location Proximity to CTA is perfect or walkable to attractions, Grant Park etc Amenities 5 stars for on site washer dryer. First time I've ever seen this at a hotel"

Find hotels in Sleepy Hollow, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Sleepy Hollow hotels

1. La Quinta Inn & Suites by Wyndham Chicago Downtown

2. Hyatt House Chicago/West Loop-Fulton Market

3. Hyatt Place Chicago/Downtown - The Loop

4. Crowne Plaza Chicago West Loop by IHG

5. Aloft by Marriott Chicago Mag Mile

6. Hilton Garden Inn Chicago Central Loop

7. River Hotel

8. L7 Chicago by LOTTE

9. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

10. Hotel Riu Plaza Chicago

11. InterContinental Chicago Magnificent Mile by IHG

12. Travelodge by Wyndham Downtown Chicago

13. Hyatt Place Chicago/River North

14. Swissotel - Chicago

15. Holiday Inn & Suites Chicago - Downtown by IHG

16. Best Western Grant Park Hotel

17. Homewood Suites by Hilton Chicago Downtown South Loop

18. Hampton Inn Chicago West Loop Fulton Market Area

19. Omni Chicago Hotel

20. The Emily Hotel

Where to stay in Sleepy Hollow

Downtown Chicago

The Loop

Magnificent Mile

River North

Theatre District

Top Sleepy Hollow Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

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