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, (2,629 reviews)
"Great stay."
Dawn
The price is SAR 753
SAR 1,025 total
includes taxes & fees
31 Aug - 1 Sep
3. Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,769 reviews)
"Great place to stay!"
Niria
The price is SAR 1,010
SAR 1,335 total
includes taxes & fees
9 Aug - 10 Aug
4. Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,525 reviews)
"Great stay in a great area of town"
Michael B
The price is SAR 1,025
SAR 1,351 total
includes taxes & fees
1 Sep - 2 Sep
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, (2,544 reviews)
"Loved the pool and the close proximity downtown!"
Macy
The price is SAR 604
SAR 718 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, (433 reviews)
"Excellent location in the city."
Adam
The price is SAR 827
SAR 983 total
includes taxes & fees
10 Aug - 11 Aug
7. Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,040 reviews)
"Great stay overall."
Rachel
The price is SAR 823
SAR 1,094 total
includes taxes & fees
2 Sep - 3 Sep
8. Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,287 reviews)
"Clean room, staff was very helpful, and location was great and certainly accessible to many locations"
Allan
The price is SAR 1,160
SAR 1,514 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, (3,329 reviews)
"Unique property, great location. Would stay here again."
Donna
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, (1,379 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, (2,589 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, (1,004 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, (4,704 reviews)
"Great stay!"
Jennifer
The price is SAR 635
SAR 755 total
includes taxes & fees
16 Aug - 17 Aug
14. Millennium Hotel Knickerbocker Chicago
Millennium Hotel Knickerbocker ChicagoStreeterville, 13.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,944 reviews)
"The location is good"
Yu
The price is SAR 638
SAR 848 total
includes taxes & fees
23 Aug - 24 Aug
15. Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,466 reviews)
"Great hotel in great location"
Emily
The price is SAR 841
SAR 1,134 total
includes taxes & fees
30 Aug - 31 Aug
16. Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,124 reviews)
"Great place to stay in Chicago."
Matthew
The price is SAR 691
SAR 933 total
includes taxes & fees
9 Aug - 10 Aug
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, (2,012 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, (1,864 reviews)
"Great location and very trendy and fun."
Shawna
The price is SAR 544
SAR 647 total
includes taxes & fees
16 Aug - 17 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, (2,079 reviews)
"Enjoyed the stay"
raj
The price is SAR 495
SAR 599 total
includes taxes & fees
31 Aug - 1 Sep
20. Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,892 reviews)
"Very nice and rooms were amazing. Loved the location and the breakfast buffet!"
Cicely
The price is SAR 822
SAR 1,085 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).
Top Sleepy Hollow Hotel Reviews
The Royal Sonesta Chicago Downtown
10/10 Excellent
