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This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

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Our top choices for Sleepy Hollow hotels

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

1. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
10.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,334 reviews)
"A great hotel in a bustling area. We had a great stay."
United States
Joel
The price is ฿8,198
฿9,746 total
includes taxes & fees
7 Sept - 8 Sept
Hyatt House Chicago/West Loop-Fulton Market
A multi-story hotel with a prominent sign reading "Crowne Plaza."

2. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,592 reviews)
"Loved our stay"
Canada
Jaclyn
The price is ฿6,405
฿7,616 total
includes taxes & fees
7 Sept - 8 Sept
Crowne Plaza Chicago West Loop by IHG
A modern hotel with a glass facade, multiple floors, and a visible entrance.

3. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,581 reviews)
"Great place to stay!"
United States
LISA
The price is ฿6,605
฿7,852 total
includes taxes & fees
7 Sept - 8 Sept
Hyatt Place Chicago/Downtown - The Loop
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

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

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,686 reviews)
"Nice place to stay"
United States
Ashraf
The price is ฿6,021
฿8,303 total
includes taxes & fees
8 Sept - 9 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

5. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (5,994 reviews)
"Room was clean, staff was friendly, breakfast was good and the location is perfect and convenient."
Mexico
Hugo
The price is ฿5,340
฿6,349 total
includes taxes & fees
10 Sept - 11 Sept
Embassy Suites by Hilton Chicago Downtown River North
A modern kitchen with a large window, a dining area, and a view of the sea.

6. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,450 reviews)
"Clean, friendly staff, quick valet, and a decent breakfast"
United States
AMBER
The price is ฿5,740
฿6,825 total
includes taxes & fees
7 Sept - 8 Sept
Homewood Suites by Hilton Chicago Downtown South Loop
A hotel lobby with a bar area, seating, and a large mirror.

7. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,409 reviews)
"Very clean, front desk staff were extremely friendly and welcoming. Beds were the most comfortable we have ever slept in when traveling!"
United States
Theresa
The price is ฿6,115
฿7,270 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Chicago Central Loop
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

8. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (5,197 reviews)
"Great location, staff & breakfast"
United States
Donna
The price is ฿4,834
฿6,693 total
includes taxes & fees
7 Sept - 8 Sept
Hotel Riu Plaza Chicago
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.

9. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (4,716 reviews)
"Great location, friendly staff."
United States
Jeff
The price is ฿8,576
฿10,196 total
includes taxes & fees
20 Sept - 21 Sept
L7 Chicago by LOTTE
A spacious lobby with a patterned carpet, comfortable seating, a fireplace, and large windows.

10. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,137 reviews)
"Very nice place would stay again"
United States
Konner
The price is ฿5,614
฿7,648 total
includes taxes & fees
10 Sept - 11 Sept
Hilton Chicago

11. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,270 reviews)
"The staff were really nice and friendly. Our room was nice and clean. I would stay here again!"
United States
Melanie
The price is ฿6,039
฿7,180 total
includes taxes & fees
7 Sept - 8 Sept
Hilton Vacation Club Hotel Blake Chicago
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

12. Carleton of Oak Park

Carleton of Oak Park
3.0 star property
9.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,147 reviews)
"Fantastic stay"
United States
Alan
The price is ฿3,385
฿3,757 total
includes taxes & fees
20 Sept - 21 Sept
Carleton of Oak Park
A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

13. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
The Loop, 11.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,911 reviews)
"Location, good stay"
United States
Shilpa
The price is ฿5,443
฿7,063 total
includes taxes & fees
7 Sept - 8 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown
A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

14. Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,909 reviews)
"Great place, comfortable beds, excellent location and wonderful breakfast buffet."
United States
Shoma
The price is ฿6,571
฿7,813 total
includes taxes & fees
10 Sept - 11 Sept
Hyatt Place Chicago/River North
A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

15. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very good, (3,004 reviews)
"Clean and the hotel was walkable distance to pretty much everything we needed."
United States
JUDY
The price is ฿5,382
฿7,375 total
includes taxes & fees
7 Sept - 8 Sept
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,002 reviews)
"Everything was fantastic and the staff went out of their way to be helpful and make sure we had a wonderful time!"
United States
Amber
The price is ฿8,267
฿9,829 total
includes taxes & fees
8 Sept - 9 Sept
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
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.

17. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,349 reviews)
"Rooms were clean and the staff was great"
United States
Odessia
The price is ฿5,119
฿6,086 total
includes taxes & fees
7 Sept - 8 Sept
Aloft by Marriott Chicago Mag Mile
A spacious bar area with high ceilings and large windows, offering views of a cityscape.

18. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,481 reviews)
"Great place to stay when available and reasonably priced."
United States
Jerry
The price is ฿6,686
฿9,133 total
includes taxes & fees
7 Sept - 8 Sept
Hyatt Regency Chicago
The Intercontinental hotel facade with a large American flag and a floral display.

19. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 13 km from Sleepy Hollow
9.2 out of 10, Wonderful, (3,256 reviews)
"Wonderfull stay"
United States
Anfal
The price is ฿8,022
฿10,702 total
includes taxes & fees
8 Sept - 9 Sept
InterContinental Chicago Magnificent Mile by IHG
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

20. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,878 reviews)
"Great location very nice rooms"
United States
susie
The price is ฿5,642
฿6,708 total
includes taxes & fees
10 Sept - 11 Sept
Hilton Chicago/Magnificent Mile Suites
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.

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.

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.

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.

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.

Top Sleepy Hollow Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Pretty comfortable and clean"
rabia 2-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown

Frequently asked questions

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.