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Check prices for these dates

This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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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, (1,186 reviews)
"Definitely a boutique hotel, but we'll maintained and in a good area with good eateries close."
United States
Brad
The price is SAR 423
SAR 469 total
includes taxes & fees
28 Oct - 29 Oct
Carleton of Oak Park
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

2. 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, (1,306 reviews)
"A great hotel in a bustling area. We had a great stay."
United States
Joel
The price is SAR 724
SAR 861 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt House Chicago/West Loop-Fulton Market
A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.

3. 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, (1,000 reviews)
"Nice place"
United States
Brock
The price is SAR 860
SAR 1,022 total
includes taxes & fees
30 Oct - 31 Oct
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
A modern interior with a bar area, seating, and decorative wooden panels.

4. 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, (2,735 reviews)
"Excellent stay at a reasonably priced hotel. Will stay again!"
United States
Shelby Ryann
The price is SAR 605
SAR 719 total
includes taxes & fees
25 Oct - 26 Oct
Best Western Grant Park Hotel
A multi-story hotel with a prominent sign reading "Crowne Plaza."

5. 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, (2,715 reviews)
"Nice hotel and location was perfect."
United States
Chriselda
The price is SAR 584
SAR 694 total
includes taxes & fees
1 Nov - 2 Nov
Crowne Plaza Chicago West Loop by IHG
An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.

6. The Emily Hotel

The Emily Hotel
4.0 star property
11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,343 reviews)
"Great modern hotel in a wonderful location! It’s within walking distance of the train station and surrounded by so many great restaurants and bars. The hotel’s restaurant was soooo yummy and incredibly convenient, too! Would definitely stay here again!"
United States
Leslie
The price is SAR 663
SAR 788 total
includes taxes & fees
1 Nov - 2 Nov
The Emily Hotel
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.

7. 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, (4,980 reviews)
"A fantastic A+ location in a well kept, boutique type hotel."
United States
Jeffrey Thomas
The price is SAR 675
SAR 803 total
includes taxes & fees
1 Nov - 2 Nov
L7 Chicago by LOTTE
A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

8. 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, (1,226 reviews)
"The room was clean and the building was nostalgic."
United States
John
The price is SAR 645
SAR 767 total
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake 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, (3,362 reviews)
"Great stay, perfect location would stay again"
United States
Kenan
The price is SAR 796
SAR 1,077 total
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.

10. The Hoxton, Chicago

The Hoxton, Chicago
4.0 star property
11.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,002 reviews)
"Great stay!"
United States
Jordan
The price is SAR 972
SAR 1,266 total
includes taxes & fees
1 Nov - 2 Nov
The Hoxton, Chicago
A modern hotel with a glass facade, multiple floors, and a visible entrance.

11. 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, (1,660 reviews)
"Great stay"
United States
Cordula
The price is SAR 732
SAR 870 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Chicago/Downtown - The Loop
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

12. 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, (2,184 reviews)
"Great place to stay at"
United States
Aran
The price is SAR 692
SAR 823 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Chicago Downtown South Loop
A modern kitchen with a large window, a dining area, and a view of the sea.

13. 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, (2,515 reviews)
"Excellent choice for a weeks stay."
United States
Jayne
The price is SAR 683
SAR 812 total
includes taxes & fees
25 Oct - 26 Oct
Homewood Suites by Hilton Chicago Downtown South Loop
A hotel lobby with a bar area, a chandelier, and a reception desk.

14. Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop
3.5 star property
Theatre District, 11.8 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,001 reviews)
"We enjoyed our stay."
United States
Karla
The price is SAR 837
SAR 995 total
includes taxes & fees
31 Oct - 1 Nov
Residence Inn Chicago Downtown/Loop
A large, historic building with a central courtyard surrounded by trees.

15. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,379 reviews)
"Friendly staff, great location"
Canada
Anna
The price is SAR 622
SAR 850 total
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A dining table set for six with a cityscape view through large windows.

16. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,546 reviews)
"Great stay"
United States
Hilary
The price is SAR 718
SAR 986 total
includes taxes & fees
31 Oct - 1 Nov
Swissotel - Chicago
A modern hotel with a glass facade, multiple floors, and a prominent sign.

17. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice location, good breakfast Comfortable beds"
United States
Terri
The price is SAR 859
SAR 1,021 total
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Chicago West Loop Fulton Market Area
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

18. 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, (2,724 reviews)
"Amazing place to stay"
United States
Shanequa
The price is SAR 860
SAR 1,152 total
includes taxes & fees
1 Nov - 2 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

19. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
River North, 12.7 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,573 reviews)
"Location and great breakfast"
United States
Catherine
The price is SAR 526
SAR 626 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Chicago Downtown
A cozy room with a sofa, a dining table, and a window with a view of buildings.

20. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
10.9 km from Sleepy Hollow
9.2 out of 10, Wonderful, (320 reviews)
"Amazing place to stay would definitely come back. Felt very cozy and a home away from home 🏠"
United States
Roland
The price is SAR 926
SAR 1,087 total
includes taxes & fees
8 Oct - 9 Oct
LIVN - West Loop 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.
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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

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

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

River Hotel

River Hotel

10/10 Excellent
"Clean and very helpful staff. Great location!"
CASEY LASHEY 3-night trip
Posted 14 hours ago
River Hotel

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.