Find hotels in Sleepy Hollow, Chicago from ￥13,395

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November 2026

December 2026

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Hilton Vacation Club Hotel Blake Chicago 4.0 star property The Loop, 11.6 km from Sleepy Hollow View	LondonHouse Chicago, Curio Collection by Hilton 4.5 star property The Loop, 12.7 km from Sleepy Hollow View	Embassy Suites by Hilton Chicago Downtown River North 4.0 star property River North, 12.9 km from Sleepy Hollow View	Hotel Riu Plaza Chicago 4.0 star property Streeterville, 13.3 km from Sleepy Hollow View	Swissotel - Chicago 4.5 star property 13 km from Sleepy Hollow View
9.6 Exceptional 1,221 reviews	9.4 Exceptional 3,896 reviews	8.6 Excellent 5,985 reviews	9.4 Exceptional 5,659 reviews	9.0 Wonderful 3,577 reviews
The price is ￥17,639 ￥20,970 total includes taxes & fees Dec 9 - Dec 10	The price is ￥22,766 ￥31,781 total includes taxes & fees Nov 23 - Nov 24	The price is ￥19,533 ￥23,222 total includes taxes & fees Dec 7 - Dec 8	The price is ￥20,910 ￥29,377 total includes taxes & fees Nov 23 - Nov 24	The price is ￥20,523 ￥29,983 total includes taxes & fees Nov 26 - Nov 27
No Breakfast included No Pool No Spa No Pet friendly Yes, WiFi included Yes, Parking	No Breakfast included No Pool Yes, Spa No Pet friendly Yes, WiFi included No Parking	Yes, Breakfast included Yes, Pool No Spa Yes, Pet friendly No WiFi included Yes, Parking	Yes, Breakfast included No Pool No Spa No Pet friendly Yes, WiFi included No Parking	No Breakfast included No Pool Yes, Spa Yes, Pet friendly No WiFi included Yes, Parking

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.

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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.

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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 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.

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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

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

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

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

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

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

Hotel Riu Plaza Chicago

Downtown Chicago

10/10 Excellent

We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...

Donna

The Intercontinental hotel facade with a large American flag and a floral display.

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

10/10 Excellent

Rosemary

A dining table set for six with a cityscape view through large windows.

Swissotel - Chicago

Downtown Chicago

10/10 Excellent

Brian

Arlo Chicago

Downtown Chicago

10/10 Excellent

Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city! The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations! I also highly recommend the lobby bar for a great happy hour spot!!! Everyone at this hotel...

Lina

A modern dining area with round tables and chairs, large windows, and a view of a cityscape.

Sofitel Chicago Magnificent Mile

Downtown Chicago

10/10 Excellent

Denine

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

Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

10/10 Excellent

Forever one of my favorite hotels and one of my two favorite Courtyard properties I've ever stayed at! This is the 3rd year in a row we've stayed here when coming to Chicago and it never disappoints. It feels like a high-end hotel for an affordable price (considering where it is)! The staff is great super helpful, rooms are so clean and overall just is one of the nicest places! Highly recommend if you're looking for a spot in Chicago!

adriana

A hotel room with a bed, a chair, a small table with flowers, and a large window with a city view.

Kinzie Hotel

Downtown Chicago

10/10 Excellent

This hotel is in a great location. It's walkable to many restaurants and other fun things to do in the city. We went to a Cubs game and were able to walk 5 minutes to the red line, which drops you off right at Wrigley field. I would definitely recommend staying here if you're going to a game but also want to stay in the city! This hotel offers amenities that others do not anymore - free breakfast and a daily complimentary happy hour! The rooms and rest of the property is kept clean, as well....

Jewel

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

Hyatt House Chicago/West Loop-Fulton Market

Downtown Chicago

10/10 Excellent

The staff was amazing and the room was super spacious and clean!! The best layout of a room for a family of 3 who enjoy separate beds and a little privacy. We had the room with two queen beds and a sofa. Amazing view of chicago from the sky deck and the pool was a nice temp! Breakfast had great options and was delicious! Rosemary seasoned potatoes and captain crunch caught my eye! The elevator was a bit hard to navigate at times as you need a key. But great safety feature so no complaints!...

Valia

A cityscape with modern skyscrapers, a waterfront, and a winter setting.

Silversmith Hotel Chicago Downtown

Downtown Chicago

10/10 Excellent

Dorothy

A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

Springhill Suites by Marriott Chicago Downtown/ River North

Downtown Chicago

10/10 Excellent

Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.

Michael

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

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

10/10 Excellent

I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable. The property is very nice, although we didn't get the two...

Joanna

Frequently Asked Questions

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.

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Find hotels in Sleepy Hollow, Chicago from ￥13,395

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Our top choices for Sleepy Hollow hotels

1. Hilton Vacation Club Hotel Blake Chicago

2. LondonHouse Chicago, Curio Collection by Hilton

3. Embassy Suites by Hilton Chicago Downtown River North

4. Hotel Riu Plaza Chicago

5. Swissotel - Chicago

6. Hotel 505 River North

7. Hyatt House Chicago/West Loop-Fulton Market

8. Courtyard by Marriott Chicago Magnificent Mile

9. Hyatt Place Chicago/River North

10. The Godfrey Hotel Chicago

11. The Royal Sonesta Chicago Downtown

12. Hilton Chicago/Magnificent Mile Suites

13. citizenM Chicago Downtown

14. Hilton Garden Inn Chicago Downtown South Loop

15. Homewood Suites by Hilton Chicago Downtown South Loop

16. L7 CHICAGO by LOTTE HOTELS

17. Hyatt Regency Chicago

18. InterContinental Chicago Magnificent Mile by IHG

19. DoubleTree by Hilton Chicago - Magnificent Mile

20. Aloft by Marriott Chicago Mag Mile

Compare top hotels in Sleepy Hollow

Hilton Vacation Club Hotel Blake Chicago

LondonHouse Chicago, Curio Collection by Hilton

Embassy Suites by Hilton Chicago Downtown River North

Hotel Riu Plaza Chicago

Swissotel - Chicago

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent

Frequently Asked Questions

What's it like in Sleepy Hollow?

If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?

Where can I learn more about changing or cancelling my trip to Sleepy Hollow?

What can I see and do in this Chicago neighborhood?

Explore a world of travel with Expedia