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, (2,643 reviews)
"Great stay."
Dawn
The price is SAR 757
SAR 1,029 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, (1,766 reviews)
"Great place to stay!"
Niria
The price is SAR 973
SAR 1,290 total
includes taxes & fees
6 Sep - 7 Sep
4. Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,543 reviews)
"Great stay"
Isaac
The price is SAR 974
SAR 1,290 total
includes taxes & fees
9 Aug - 10 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, (2,555 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, (438 reviews)
"Excellent location in the city."
Adam
The price is SAR 763
SAR 907 total
includes taxes & fees
31 Aug - 1 Sep
7. 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, (2,970 reviews)
"Perfect destination for family"
Mohana Sandeep
The price is SAR 667
SAR 903 total
includes taxes & fees
31 Aug - 1 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, (2,305 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, (3,345 reviews)
"Great location"
Jasmin
The price is SAR 676
SAR 804 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, (1,384 reviews)
"Awesome hotel I enjoyed my stay"
Adam
The price is SAR 558
SAR 655 total
includes taxes & fees
31 Aug - 1 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, (2,603 reviews)
"Very nice place to stay and close to everything!"
Sally
The price is SAR 646
SAR 768 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, (1,009 reviews)
"Absolutely a fantastic location, with great staff and a very comfortable stay."
Jeffrey
The price is SAR 603
SAR 717 total
includes taxes & fees
30 Aug - 31 Aug
13. Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,737 reviews)
"Great stay!"
Jennifer
The price is SAR 603
SAR 717 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, (1,953 reviews)
"Nice Hotel, enjoyed our stay"
Anita
The price is SAR 638
SAR 848 total
includes taxes & fees
30 Aug - 31 Aug
15. Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,490 reviews)
"Great hotel in great location"
Emily
The price is SAR 905
SAR 1,210 total
includes taxes & fees
31 Aug - 1 Sep
16. Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,132 reviews)
"Great place to stay in Chicago."
Matthew
The price is SAR 672
SAR 911 total
includes taxes & fees
31 Aug - 1 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, (2,026 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, (1,897 reviews)
"Great location and very trendy and fun."
Shawna
The price is SAR 514
SAR 611 total
includes taxes & fees
31 Aug - 1 Sep
19. Hotel Saint Clair- Magnificent Mile
Hotel Saint Clair- Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very Good, (2,097 reviews)
"Enjoyed the stay"
raj
The price is SAR 546
SAR 660 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, (4,935 reviews)
"Very nice and rooms were amazing. Loved the location and the breakfast buffet!"
Cicely
The price is SAR 745
SAR 993 total
includes taxes & fees
1 Sep - 2 Sep
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 Chicago Hotel Collection Ambassador Gold Coast
10/10 Excellent
