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Check prices for these dates

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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, (1,212 reviews)
"Definitely a boutique hotel, but we'll maintained and in a good area with good eateries close."
United States
Brad
The price is 3.163.918 ₫
3.511.329 ₫ total
includes taxes & fees
5 Nov - 6 Nov
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 3.711.054 ₫
5.180.377 ₫ total
includes taxes & fees
22 Nov - 23 Nov
LondonHouse Chicago, Curio Collection by Hilton
A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

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 3.205.276 ₫
3.685.426 ₫ total
includes taxes & fees
1 Nov - 2 Nov
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 4.046.232 ₫
5.546.833 ₫ total
includes taxes & fees
23 Nov - 24 Nov
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 4.141.190 ₫
4.923.185 ₫ total
includes taxes & fees
25 Nov - 26 Nov
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 3.745.671 ₫
4.453.227 ₫ total
includes taxes & fees
22 Nov - 23 Nov
L7 Chicago by LOTTE
A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

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 5.143.951 ₫
7.038.166 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Fairmont Chicago at Millennium Park
A cityscape with modern high-rise buildings, a river, and a boat.

8. 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 4.520.950 ₫
6.296.454 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Hyatt Regency Chicago
The Intercontinental hotel facade with a large American flag and a floral display.

9. 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 4.859.612 ₫
6.682.308 ₫ total
includes taxes & fees
26 Nov - 27 Nov
InterContinental Chicago Magnificent Mile by IHG
A room with two chairs and a small table, a large window with a city view at night.

10. 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 3.722.256 ₫
4.425.391 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Eurostars Magnificent Mile
A cityscape with tall buildings, a river, and a bridge.

11. 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 3.332.586 ₫
4.788.800 ₫ total
includes taxes & fees
26 Nov - 27 Nov
The Royal Sonesta Chicago Downtown
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

12. 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 3.273.776 ₫
3.892.192 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Embassy Suites by Hilton Chicago Downtown River North
A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

13. 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 3.012.701 ₫
4.492.201 ₫ total
includes taxes & fees
26 Nov - 27 Nov
Swissotel - Chicago
A multi-story hotel with a modern glass facade, located in an urban setting with a parking lot and street views.

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 3.076.031 ₫
3.657.093 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Hyatt Place Chicago/River North
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

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 2.875.324 ₫
4.245.361 ₫ total
includes taxes & fees
25 Nov - 26 Nov
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 2.996.744 ₫
3.562.828 ₫ total
includes taxes & fees
23 Nov - 24 Nov
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 2.962.295 ₫
3.521.875 ₫ total
includes taxes & fees
23 Nov - 24 Nov
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 4.071.734 ₫
5.639.877 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Radisson Blu Aqua Hotel Chicago
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

19. 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 3.054.059 ₫
3.630.969 ₫ total
includes taxes & fees
23 Nov - 24 Nov
Hilton Chicago/Magnificent Mile Suites
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.

20. 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 2.829.690 ₫
3.364.219 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Aloft by Marriott Chicago Mag Mile
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 top hotels in Sleepy Hollow

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
9.6 km from Sleepy Hollow
View
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
The Loop, 12.7 km from Sleepy Hollow
View
A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

Hampton Inn Chicago-O'Hare International Airport

2.5 star property
19.4 km from Sleepy Hollow
View
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

Hotel Riu Plaza Chicago

4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
View
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

4.0 star property
The Loop, 11.6 km from Sleepy Hollow
View
9.2
Wonderful
1,212 reviews
9.4
Exceptional
3,870 reviews
9.4
Exceptional
2,408 reviews
9.4
Exceptional
5,610 reviews
9.6
Exceptional
1,213 reviews
The price is 3.163.918 ₫
3.511.329 ₫ total
includes taxes & fees
5 Nov - 6 Nov
The price is 3.711.054 ₫
5.180.377 ₫ total
includes taxes & fees
22 Nov - 23 Nov
The price is 3.205.276 ₫
3.685.426 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The price is 4.046.232 ₫
5.546.833 ₫ total
includes taxes & fees
23 Nov - 24 Nov
The price is 4.141.190 ₫
4.923.185 ₫ total
includes taxes & fees
25 Nov - 26 Nov
  • 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
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • No Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

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 6 hours ago
The Wade

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.