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Our top choices for Sleepy Hollow hotels

1. 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, (1,484 reviews)
"Enjoyed my stay!"
United States
Kimberly
The price is ₩295,314
₩351,098 total
includes taxes & fees
Aug 9 - Aug 10
Hyatt Place Chicago/Downtown - The Loop

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, (2,436 reviews)
"Great location"
United States
Navin
The price is ₩256,603
₩305,090 total
includes taxes & fees
Aug 20 - Aug 21
Crowne Plaza Chicago West Loop by IHG

3. 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, (2,397 reviews)
"Great stay"
United Kingdom
jayne
The price is ₩279,126
₩331,854 total
includes taxes & fees
Aug 17 - Aug 18
Homewood Suites by Hilton Chicago Downtown South Loop

4. 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, (2,846 reviews)
"Location is very good and staff is nice!"
United States
Diana
The price is ₩265,199
₩341,434 total
includes taxes & fees
Aug 9 - Aug 10
La Quinta Inn & Suites by Wyndham Chicago Downtown

5. 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, (4,855 reviews)
"We were very happy with our stay."
United States
Deanne
The price is ₩312,551
₩413,052 total
includes taxes & fees
Aug 23 - Aug 24
Hotel Riu Plaza Chicago

6. 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, (2,550 reviews)
"Loved the pool and the close proximity downtown!"
United States
Macy
The price is ₩279,196
₩331,935 total
includes taxes & fees
Aug 9 - Aug 10
DoubleTree by Hilton Chicago - Magnificent Mile

7. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,294 reviews)
"Very helpful front desk staff and friendly cleaners. Very pleasant stay"
United States
Aleace
The price is ₩289,786
₩344,526 total
includes taxes & fees
Aug 19 - Aug 20
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

8. 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, (4,459 reviews)
"Great stay"
United States
Julie Ann
The price is ₩288,949
₩343,534 total
includes taxes & fees
Aug 17 - Aug 18
L7 Chicago by LOTTE

9. 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
8.2 out of 10, Very Good, (2,964 reviews)
"Perfect destination for family"
United States
Mohana Sandeep
The price is ₩269,158
₩363,029 total
includes taxes & fees
Aug 10 - Aug 11
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

10. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,672 reviews)
"Great location"
United States
Dee
The price is ₩299,064
₩392,229 total
includes taxes & fees
Aug 13 - Aug 14
Hyatt Centric The Loop Chicago

11. 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, (1,899 reviews)
"Great location, good breakfast and super nice staff"
United States
Michelle
The price is ₩249,220
₩296,299 total
includes taxes & fees
Aug 9 - Aug 10
Hyatt Place Chicago/River North

12. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 13.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,586 reviews)
"Very nice place to stay and close to everything!"
United States
Sally
The price is ₩268,838
₩319,621 total
includes taxes & fees
Aug 11 - Aug 12
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

13. 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, (3,333 reviews)
"Unique property, great location. Would stay here again."
United States
Donna
The price is ₩272,038
₩323,427 total
includes taxes & fees
Aug 9 - Aug 10
Aloft by Marriott Chicago Mag Mile

14. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very Good, (1,855 reviews)
"Great stay"
United States
Judy
The price is ₩260,997
₩310,298 total
includes taxes & fees
Aug 9 - Aug 10
The Chicago Hotel Collection Ambassador Gold Coast

15. 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, (2,634 reviews)
"Nice Stay"
United States
Morgan
The price is ₩319,002
₩429,809 total
includes taxes & fees
Aug 23 - Aug 24
Sable at Navy Pier Chicago, Curio Collection by Hilton

16. 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, (2,119 reviews)
"helpful staff, great location, comfortable rooms and great views"
United States
Jordan Leigh
The price is ₩263,484
₩313,257 total
includes taxes & fees
Aug 9 - Aug 10
Hilton Garden Inn Chicago Downtown South Loop

17. 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, (4,675 reviews)
"Great stay!"
United States
Jennifer
The price is ₩273,027
₩324,604 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Chicago/Magnificent Mile Suites

18. 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)
"It’s a clean and well managed hotel."
United States
Jihi
The price is ₩323,986
₩385,186 total
includes taxes & fees
Aug 16 - Aug 17
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

19. River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,373 reviews)
"Nice hotel a lot of things to do around"
United States
yenedit
The price is ₩302,690
₩359,862 total
includes taxes & fees
Aug 23 - Aug 24
River Hotel

20. 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)
"Great hotel in great location"
United States
Emily
The price is ₩427,697
₩560,380 total
includes taxes & fees
Aug 23 - Aug 24
Hyatt Regency 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.

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most.

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.

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.

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.

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.

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

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 Works Museum, and Jedlica Performing Arts Center are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Los Globos and Balzekas Museum of Lithuanian Culture are also worth a stop.