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Chicago Hotel Guide. Hotels in Sleepy Hollow, Chicago, United States of America

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Check prices for these dates

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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Our top choices for Sleepy Hollow hotels

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

1. Carleton of Oak Park

Carleton of Oak Park
3.0 star property
9.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,209 reviews)
"Definitely a boutique hotel, but we'll maintained and in a good area with good eateries close."
United States
Brad
The price is €122
includes taxes & fees
4 Nov - 5 Nov
Carleton of Oak Park
A modern hotel lobby with seating areas, a reception desk, and an elevator.

2. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,737 reviews)
"Room was dated but clean, staff was friendly, location was perfect for my needs"
United States
Michelle
The price is €104
includes taxes & fees
23 Nov - 24 Nov
Best Western Grant Park Hotel
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

3. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,203 reviews)
"Great place to stay at"
United States
Aran
The price is €104
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Chicago Downtown South Loop
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

4. 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, (1,316 reviews)
"Location was amazing. Loved the outdoor market in walking distance"
United States
Georgianna
The price is €147
includes taxes & fees
23 Nov - 24 Nov
Hyatt House Chicago/West Loop-Fulton Market
A modern kitchen with a large window, a dining area, and a view of the sea.

5. 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, (2,532 reviews)
"Wonderful room and great breakfast buffet!"
United States
Nicole
The price is €113
includes taxes & fees
23 Nov - 24 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

6. 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, (2,762 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is €170
includes taxes & fees
23 Nov - 24 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

7. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,435 reviews)
"Convenient location near good restaurants."
United States
Scott
The price is €125
includes taxes & fees
22 Nov - 23 Nov
Claridge House Chicago, Tapestry Collection by Hilton
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

8. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,003 reviews)
"Room was standard, close to millennium park, very helpful staff, & yummy restaurant!"
United States
Caitlin Vania
The price is €136
includes taxes & fees
23 Nov - 24 Nov
Le Méridien Essex Chicago
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

9. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,132 reviews)
"It was a wonderful stay!"
United States
Ashya
The price is €124
includes taxes & fees
10 Nov - 11 Nov
Congress Plaza Hotel
Bar (on property)

10. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 12.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,971 reviews)
"Hotel is great for the price."
United States
alex
The price is €108
includes taxes & fees
23 Nov - 24 Nov
ACME Hotel Chicago, Outset Collection by Hilton
A building with a stone facade and large glass windows.

11. Ohio House Motel

Ohio House Motel
3.0 star property
River North, 12.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,233 reviews)
"The location was great and hotel was cute and had everything we needed."
United States
Colin
The price is €105
includes taxes & fees
22 Nov - 23 Nov
Ohio House Motel
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

12. Hotel 505 River North

Hotel 505 River North
4.5 star property
River North, 12.8 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,982 reviews)
"Great stay!"
United States
Miya
The price is €147
includes taxes & fees
23 Nov - 24 Nov
Hotel 505 River North
A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.

13. Level Chicago Fulton Market

Level Chicago Fulton Market
4.0 star property
West Loop, 11.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (593 reviews)
"Good locations"
United States
Trang
The price is €150
includes taxes & fees
22 Nov - 23 Nov
Level Chicago Fulton Market
A modern hotel lobby with a bar area, seating arrangements, and a television screen.

14. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,712 reviews)
"Amazing location everything is close by"
United States
Vansh
The price is €119
includes taxes & fees
23 Nov - 24 Nov
Cambria Hotel Chicago Loop - Theatre District
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

15. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,579 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is €108
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
A luxurious bathroom with a large oval bathtub, a chandelier, and two large mirrors with floral arrangements.

16. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.5 km from Sleepy Hollow
8.4 out of 10, Very good, (3,952 reviews)
"Hotel Staff was amazing. Would definitely stay again."
United States
Benjamin
The price is €91
includes taxes & fees
23 Nov - 24 Nov
The Whitehall Hotel, BW Premier Collection
A spacious lobby with a grand chandelier, a staircase, and a seating area with two chairs and a table.

17. Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 13.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,915 reviews)
"Terrific location for Michigan Ave (1/2 block)and Oak St Beach (short walk.)"
United States
Richard
The price is €118
includes taxes & fees
26 Nov - 27 Nov
Millennium Hotel Knickerbocker Chicago
A modern interior with a geometric bookshelf filled with books, a bench, and a lamp.

18. Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,414 reviews)
"Outstanding hotel highly recommend staying here!!!!"
United States
Daniel
The price is €155
includes taxes & fees
26 Nov - 27 Nov
Arlo Chicago
A modern building with a colorful facade and a red circular seating area.

19. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,379 reviews)
"Absolutely loved it would stay again"
United States
Katarina
The price is €123
includes taxes & fees
23 Nov - 24 Nov
citizenM Chicago Downtown
A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

20. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,563 reviews)
"Good location and nice hotel"
United States
Oleg
The price is €156
includes taxes & fees
26 Nov - 27 Nov
Swissotel - Chicago
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.
View all properties

Compare popular hotels in Sleepy Hollow

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."
Carleton of Oak Park
3.0 star property
9.2
Wonderful
1,209 reviews
View
A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4
Exceptional
2,762 reviews
View
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.
Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
9.0
Wonderful
1,316 reviews
View
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8
Excellent
2,203 reviews
View
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.
Le Méridien Essex Chicago
4.0 star property
9.0
Wonderful
1,003 reviews
View

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas 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.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

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

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 large, historic building with a central tower and multiple windows, located near a body of water.

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

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

8/10 Good
"Solid hotel in a great location. We were there as they were transferring to a full launch of the SI branded hotel. Good gym, rooms are well appointed. During our visit they had an all inclusive rooftop bar from 3-7pm every day which was a great touch but nobody actually told us about it, we kind of found it ourselves. Good option for a hotel in downtown Chicago though!"
Kris 3-night trip
Posted 1 hour ago
Sports Illustrated Resorts Chicago

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.