Find hotels in Sleepy Hollow, Chicago
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Our top choices for Sleepy Hollow hotels
1. 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, (2,641 reviews)
"Great stay."
Dawn
The price is SAR 782
SAR 1,059 total
includes taxes & fees
30 Aug - 31 Aug
3. Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,777 reviews)
"Great place to stay!"
Niria
The price is SAR 1,048
SAR 1,380 total
includes taxes & fees
9 Aug - 10 Aug
4. Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,534 reviews)
"Great stay"
Isaac
The price is SAR 1,003
SAR 1,324 total
includes taxes & fees
23 Aug - 24 Aug
5. 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 SAR 653
SAR 776 total
includes taxes & fees
30 Aug - 31 Aug
6. Hilton Grand Vacations Club Chicago Magnificent Mile
Hilton Grand Vacations Club Chicago Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (434 reviews)
"Excellent location in the city."
Adam
The price is SAR 827
SAR 983 total
includes taxes & fees
31 Aug - 1 Sep
7. Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,048 reviews)
"Great stay overall."
Rachel
The price is SAR 856
SAR 1,134 total
includes taxes & fees
30 Aug - 31 Aug
8. Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,298 reviews)
"Clean room, staff was very helpful, and location was great and certainly accessible to many locations"
Allan
The price is SAR 1,198
SAR 1,558 total
includes taxes & fees
2 Sep - 3 Sep
9. Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,342 reviews)
"Great location"
Jasmin
The price is SAR 710
SAR 844 total
includes taxes & fees
16 Aug - 17 Aug
10. Ivy Boutique Hotel
Ivy Boutique HotelStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,381 reviews)
"Awesome hotel I enjoyed my stay"
Adam
The price is SAR 549
SAR 645 total
includes taxes & fees
1 Sep - 2 Sep
11. 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, (2,598 reviews)
"Very nice place to stay and close to everything!"
Sally
The price is SAR 691
SAR 822 total
includes taxes & fees
30 Aug - 31 Aug
12. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Fairfield Inn & Suites Chicago Downtown / Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,008 reviews)
"Absolutely a fantastic location, with great staff and a very comfortable stay."
Jeffrey
The price is SAR 674
SAR 802 total
includes taxes & fees
9 Aug - 10 Aug
13. Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,730 reviews)
"Great location, rooms very comfortable and with a great size"
CHRISTIAN GIOVANNI
The price is SAR 653
SAR 776 total
includes taxes & fees
30 Aug - 31 Aug
14. Millennium Hotel Knickerbocker Chicago
Millennium Hotel Knickerbocker ChicagoStreeterville, 13.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,950 reviews)
"Nice Hotel, enjoyed our stay"
Anita
The price is SAR 638
SAR 848 total
includes taxes & fees
24 Aug - 25 Aug
15. Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,481 reviews)
"Great hotel in great location"
Emily
The price is SAR 905
SAR 1,210 total
includes taxes & fees
1 Sep - 2 Sep
16. Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,130 reviews)
"Great place to stay in Chicago."
Matthew
The price is SAR 691
SAR 933 total
includes taxes & fees
1 Sep - 2 Sep
17. Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,024 reviews)
"Great location, great staff, and comfy hotel."
Zachary
The price is SAR 695
SAR 826 total
includes taxes & fees
30 Aug - 31 Aug
18. The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent MileStreeterville, 13.5 km from Sleepy Hollow
7.8 out of 10, Good, (1,881 reviews)
"Great location and very trendy and fun."
Shawna
The price is SAR 544
SAR 647 total
includes taxes & fees
24 Aug - 25 Aug
19. Hotel Saint Clair- Magnificent Mile
Hotel Saint Clair- Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very Good, (2,090 reviews)
"Enjoyed the stay"
raj
The price is SAR 511
SAR 617 total
includes taxes & fees
11 Aug - 12 Aug
20. Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,921 reviews)
"Very nice and rooms were amazing. Loved the location and the breakfast buffet!"
Cicely
The price is SAR 785
SAR 1,040 total
includes taxes & fees
30 Aug - 31 Aug
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
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
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.
Photo by Mattyboy876
Open Photo by Mattyboy876
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
