Find hotels in Sleepy Hollow, Chicago
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Our top choices for Sleepy Hollow hotels
1. Hyatt Place Chicago/Downtown - The Loop
Hyatt Place Chicago/Downtown - The LoopThe Loop, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,484 reviews)
"Enjoyed my stay!"
Kimberly
The price is ₩295,314
₩351,098 total
includes taxes & fees
Aug 9 - Aug 10
2. Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,436 reviews)
"Great location"
Navin
The price is ₩256,603
₩305,090 total
includes taxes & fees
Aug 20 - Aug 21
3. Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South LoopThe Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,397 reviews)
"Great stay"
jayne
The price is ₩279,126
₩331,854 total
includes taxes & fees
Aug 17 - Aug 18
4. La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago DowntownThe Loop, 11.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,846 reviews)
"Location is very good and staff is nice!"
Diana
The price is ₩265,199
₩341,434 total
includes taxes & fees
Aug 9 - Aug 10
5. Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,855 reviews)
"We were very happy with our stay."
Deanne
The price is ₩312,551
₩413,052 total
includes taxes & fees
Aug 23 - Aug 24
6. DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,550 reviews)
"Loved the pool and the close proximity downtown!"
Macy
The price is ₩279,196
₩331,935 total
includes taxes & fees
Aug 9 - Aug 10
7. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection HotelThe 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"
Aleace
The price is ₩289,786
₩344,526 total
includes taxes & fees
Aug 19 - Aug 20
8. L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (4,459 reviews)
"Great stay"
Julie Ann
The price is ₩288,949
₩343,534 total
includes taxes & fees
Aug 17 - Aug 18
9. Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,964 reviews)
"Perfect destination for family"
Mohana Sandeep
The price is ₩269,158
₩363,029 total
includes taxes & fees
Aug 10 - Aug 11
10. Hyatt Centric The Loop Chicago
Hyatt Centric The Loop ChicagoTheatre District, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,672 reviews)
"Great location"
Dee
The price is ₩299,064
₩392,229 total
includes taxes & fees
Aug 13 - Aug 14
11. Hyatt Place Chicago/River North
Hyatt Place Chicago/River NorthRiver North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,899 reviews)
"Great location, good breakfast and super nice staff"
Michelle
The price is ₩249,220
₩296,299 total
includes taxes & fees
Aug 9 - Aug 10
12. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Sonesta ES Suites Chicago Downtown Magnificent Mile - MedicalStreeterville, 13.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,586 reviews)
"Very nice place to stay and close to everything!"
Sally
The price is ₩268,838
₩319,621 total
includes taxes & fees
Aug 11 - Aug 12
13. Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,333 reviews)
"Unique property, great location. Would stay here again."
Donna
The price is ₩272,038
₩323,427 total
includes taxes & fees
Aug 9 - Aug 10
14. The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very Good, (1,855 reviews)
"Great stay"
Judy
The price is ₩260,997
₩310,298 total
includes taxes & fees
Aug 9 - Aug 10
15. Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by HiltonStreeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,634 reviews)
"Nice Stay"
Morgan
The price is ₩319,002
₩429,809 total
includes taxes & fees
Aug 23 - Aug 24
16. Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South LoopThe 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"
Jordan Leigh
The price is ₩263,484
₩313,257 total
includes taxes & fees
Aug 9 - Aug 10
17. Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,675 reviews)
"Great stay!"
Jennifer
The price is ₩273,027
₩324,604 total
includes taxes & fees
Aug 16 - Aug 17
18. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,000 reviews)
"It’s a clean and well managed hotel."
Jihi
The price is ₩323,986
₩385,186 total
includes taxes & fees
Aug 16 - Aug 17
19. River Hotel
River HotelThe 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"
yenedit
The price is ₩302,690
₩359,862 total
includes taxes & fees
Aug 23 - Aug 24
20. Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,510 reviews)
"Great hotel in great location"
Emily
The price is ₩427,697
₩560,380 total
includes taxes & fees
Aug 23 - Aug 24
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.
