What's it like in Sleepy Hollow?

Sleepy Hollow is a neighbourhood that travellers 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 reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of your booking. Put your dates in and click on "Search", then filter by "fully refundable" to view the top deals on offer in Sleepy Hollow.

What can I see and do in this Chicago neighbourhood?

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.

The Best Hotels in Sleepy Hollow, Chicago - 2026 Updated Prices

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Our top choices for Sleepy Hollow hotels

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

1. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

LISA

Rp3.565.199 total

includes taxes & fees

7 Sept - 8 Sept

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 14.4 km from Sleepy Hollow

Ashraf

Rp4.155.915 total

includes taxes & fees

30 Aug - 31 Aug

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

3. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Peter

Rp4.090.205 total

includes taxes & fees

30 Aug - 31 Aug

A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

4. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

MAGALY

Rp3.351.309 total

includes taxes & fees

1 Sept - 2 Sept

An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

5. Hyatt Centric The Loop Chicago

Theatre District, 11.8 km from Sleepy Hollow

Tamika

Rp3.970.398 total

includes taxes & fees

30 Aug - 31 Aug

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

6. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

susie

Rp3.351.286 total

includes taxes & fees

1 Sept - 2 Sept

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

7. Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Abdulsamad

Rp5.295.107 total

includes taxes & fees

30 Aug - 31 Aug

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

8. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Hugo

Rp3.209.732 total

includes taxes & fees

7 Sept - 8 Sept

9. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Streeterville, 13.9 km from Sleepy Hollow

Belle

Rp3.307.825 total

includes taxes & fees

7 Sept - 8 Sept

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

10. The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 13.9 km from Sleepy Hollow

Alma

Rp3.016.071 total

includes taxes & fees

31 Aug - 1 Sept

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

11. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Shoma

Rp3.586.292 total

includes taxes & fees

7 Sept - 8 Sept

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

12. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

AMBER

Rp3.478.706 total

includes taxes & fees

8 Sept - 9 Sept

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

Girivasan

Rp4.727.576 total

includes taxes & fees

30 Aug - 31 Aug

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

14. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Jaclyn

Rp3.747.710 total

includes taxes & fees

30 Aug - 31 Aug

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

15. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.6 km from Sleepy Hollow

Shilpa

Rp2.955.465 total

includes taxes & fees

30 Aug - 31 Aug

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.

16. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Odessia

Rp3.248.760 total

includes taxes & fees

7 Sept - 8 Sept

17. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

Melanie

Rp3.823.283 total

includes taxes & fees

9 Sept - 10 Sept

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

Rp3.586.294 total

includes taxes & fees

7 Sept - 8 Sept

A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

19. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Rajiv

Rp3.872.072 total

includes taxes & fees

1 Sept - 2 Sept

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

20. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Patrick

Rp4.535.607 total

includes taxes & fees

7 Sept - 8 Sept

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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas 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

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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