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Oct 30 - Nov 1
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Nov 6 - Nov 8

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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, (1,212 reviews)
"Definitely a boutique hotel, but we'll maintained and in a good area with good eateries close."
United States
Brad
The price is ₩162,493
₩180,335 total
includes taxes & fees
Nov 5 - Nov 6
Carleton of Oak Park
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

2. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,870 reviews)
"It was a very nice stay! We enjoyed the hotel The views were amazing"
United States
James
The price is ₩190,704
₩266,211 total
includes taxes & fees
Nov 22 - Nov 23
LondonHouse Chicago, Curio Collection by Hilton
A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

3. Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport
2.5 star property
19.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,408 reviews)
"Staff was helpful, room was clean and the shuttle was easy to catch coming from and going to the airport."
Canada
Jaime
The price is ₩164,617
₩189,276 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Chicago-O'Hare International Airport
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

4. 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, (5,610 reviews)
"All the stay was perfect, location is near to all the best places"
Mexico
JESUS VERA
The price is ₩169,519
₩239,377 total
includes taxes & fees
Nov 24 - Nov 25
Hotel Riu Plaza Chicago
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

5. 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, (1,213 reviews)
"Great location !"
Canada
Josee
The price is ₩212,808
₩252,993 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Vacation Club Hotel Blake Chicago
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.

6. 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, (5,129 reviews)
"Amazing hotel will stay again"
United States
Matthew
The price is ₩192,483
₩228,842 total
includes taxes & fees
Nov 22 - Nov 23
L7 Chicago by LOTTE
A modern kitchen with a marble island, fruit bowls, and a city view.

7. Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,311 reviews)
"Beautiful hotel and great location."
United States
Ruby
The price is ₩264,184
₩361,468 total
includes taxes & fees
Nov 24 - Nov 25
Fairmont Chicago at Millennium Park
A room with two chairs and a small table, a large window with a city view at night.

8. Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,969 reviews)
"Nice rooms and great location"
United States
Gabriela
The price is ₩200,727
₩238,643 total
includes taxes & fees
Nov 22 - Nov 23
Eurostars Magnificent Mile
A spacious bar area with high ceilings and large windows, offering views of a cityscape.

9. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,510 reviews)
"Wonderful will stay again"
United States
Kristee
The price is ₩232,323
₩323,564 total
includes taxes & fees
Nov 24 - Nov 25
Hyatt Regency Chicago
A dining area with a table set for four, large windows offering a cityscape view at dusk.

10. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,667 reviews)
"Location of hotel and room view of river was outstanding!"
United States
Scott
The price is ₩171,255
₩246,088 total
includes taxes & fees
Nov 26 - Nov 27
The Royal Sonesta Chicago Downtown
The Intercontinental hotel facade with a large American flag and a floral display.

11. 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, (3,407 reviews)
"Nice stay good staff, great location"
United States
Nellie
The price is ₩251,907
₩346,391 total
includes taxes & fees
Nov 26 - Nov 27
InterContinental Chicago Magnificent Mile by IHG
A dining table set for six with a cityscape view through large windows.

12. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,566 reviews)
"Good location and nice hotel"
United States
Oleg
The price is ₩156,168
₩232,859 total
includes taxes & fees
Nov 26 - Nov 27
Swissotel - Chicago
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

13. 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, (5,976 reviews)
"I’d stay here again."
United States
Eliana
The price is ₩168,507
₩200,338 total
includes taxes & fees
Nov 24 - Nov 25
Embassy Suites by Hilton Chicago Downtown River North
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, (1,920 reviews)
"Great location, clean hotel and overall a great place to stay."
United States
Pamela
The price is ₩157,980
₩187,820 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt Place Chicago/River North
A modern restaurant interior with a green wall, hanging lights, and a long dining area.

15. 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, (2,986 reviews)
"Great stay!"
United States
Miya
The price is ₩147,757
₩218,158 total
includes taxes & fees
Nov 22 - Nov 23
Hotel 505 River North
A modern building with a colorful facade and a red circular seating area.

16. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,383 reviews)
"Absolutely loved it would stay again"
United States
Katarina
The price is ₩155,432
₩184,793 total
includes taxes & fees
Nov 23 - Nov 24
citizenM Chicago Downtown
A hotel room with a large window offering a city view, a bed, a desk, and a chair.

17. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,100 reviews)
"Great location Staff was terrific"
United States
Richard
The price is ₩152,138
₩180,877 total
includes taxes & fees
Nov 24 - Nov 25
Courtyard by Marriott Chicago Magnificent Mile
Exterior

18. Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,160 reviews)
"Loved the hotel!"
United States
Shannon
The price is ₩209,117
₩289,656 total
includes taxes & fees
Nov 22 - Nov 23
Radisson Blu Aqua Hotel Chicago
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.

19. 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, (3,328 reviews)
"Stayed during Lollapalooza and loved it."
United States
Jena
The price is ₩145,328
₩172,781 total
includes taxes & fees
Nov 22 - Nov 23
Aloft by Marriott Chicago Mag Mile
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, (5,037 reviews)
"Great place to stay"
United States
Melissa
The price is ₩156,851
₩186,480 total
includes taxes & fees
Nov 24 - Nov 25
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.
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
1,212 reviews
View
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4
Exceptional
2,765 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
1,310 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
2,197 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
1,001 reviews
View

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.

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

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.

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.

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.

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.

Top Sleepy Hollow Hotel Reviews

The Wade

The Wade

8/10 Good
"The room was clean and there are no amenities at all. No water, no coffee, no tea, no shower cap, nothing…. Just a room. Hours for restaurant not as advertised. Good location."
Vonda 3-night trip
Posted 4 hours ago
The Wade

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.