Find hotels in Sleepy Hollow, Chicago
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Our top choices for Sleepy Hollow hotels
1. Carleton of Oak Park
Carleton of Oak Park9.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,170 reviews)
"Rooms were clean and the staff was amazing!"
Suzanne
The price is SAR 423
SAR 469 total
includes taxes & fees
6 Oct - 7 Oct
2. Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,292 reviews)
"Great stay!"
Alan
The price is SAR 603
SAR 827 total
includes taxes & fees
24 Oct - 25 Oct
3. 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, (2,720 reviews)
"Amazing place to stay"
Shanequa
The price is SAR 1,194
SAR 1,549 total
includes taxes & fees
22 Oct - 23 Oct
4. Hyatt House Chicago/West Loop-Fulton Market
Hyatt House Chicago/West Loop-Fulton Market10.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,307 reviews)
"A great hotel in a bustling area. We had a great stay."
Joel
The price is SAR 987
SAR 1,174 total
includes taxes & fees
4 Oct - 5 Oct
5. 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, (2,676 reviews)
"Great stay, close to great food and ambiance in West Loop."
Victoria
The price is SAR 657
SAR 782 total
includes taxes & fees
25 Oct - 26 Oct
6. Hampton Inn Chicago West Loop Fulton Market Area
Hampton Inn Chicago West Loop Fulton Market Area11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,005 reviews)
"Hotel was clean, the room was comfortable and spacious, the amenities were nice, and the breakfast was good. Would stay again."
Rebecca
The price is SAR 850
SAR 1,010 total
includes taxes & fees
25 Oct - 26 Oct
7. Residence Inn Chicago Downtown/Loop
Residence Inn Chicago Downtown/LoopTheatre District, 11.8 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,004 reviews)
"We enjoyed our stay."
Karla
The price is SAR 987
SAR 1,174 total
includes taxes & fees
24 Oct - 25 Oct
8. Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,489 reviews)
"Really great stay and experience"
Whitney
The price is SAR 1,186
SAR 1,544 total
includes taxes & fees
25 Oct - 26 Oct
9. 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, (2,162 reviews)
"Great place to stay at"
Aran
The price is SAR 702
SAR 835 total
includes taxes & fees
25 Oct - 26 Oct
10. 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, (2,486 reviews)
"Great overall stay within walking distance of so much."
Cecilia
The price is SAR 785
SAR 933 total
includes taxes & fees
25 Oct - 26 Oct
11. L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (4,893 reviews)
"Excelent location, Good service and Great Restaurant."
GUILLERMO
The price is SAR 1,024
SAR 1,217 total
includes taxes & fees
24 Oct - 25 Oct
12. Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,971 reviews)
"Very nice hotel, friendly staff, good location"
Brian
The price is SAR 654
SAR 778 total
includes taxes & fees
25 Oct - 26 Oct
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, (3,351 reviews)
"I really liked the location of the hotel."
Carmina
The price is SAR 815
SAR 969 total
includes taxes & fees
25 Oct - 26 Oct
14. Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,839 reviews)
"Quick check in process, great location, helpful staff"
Brandi
The price is SAR 1,178
SAR 1,534 total
includes taxes & fees
3 Oct - 4 Oct
15. LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonThe Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,863 reviews)
"Great location! Would stay again!"
Sharee
The price is SAR 941
SAR 1,231 total
includes taxes & fees
25 Oct - 26 Oct
16. 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, (1,633 reviews)
"Perfect location and great accommodations! Would stay again!"
Lauren
The price is SAR 796
SAR 946 total
includes taxes & fees
25 Oct - 26 Oct
17. Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoThe Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,244 reviews)
"The room was clean and the building was nostalgic."
John
The price is SAR 1,186
SAR 1,410 total
includes taxes & fees
14 Oct - 15 Oct
18. LIVN - West Loop Chicago
LIVN - West Loop Chicago10.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (295 reviews)
"It was a very nice place to stay"
chidubem
The price is SAR 754
SAR 885 total
includes taxes & fees
1 Oct - 2 Oct
19. The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 13.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,361 reviews)
"Loved my stay the staff was nice and the location was great."
Marta
The price is SAR 672
SAR 799 total
includes taxes & fees
14 Oct - 15 Oct
20. 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, (1,001 reviews)
"Nice place"
Brock
The price is SAR 849
SAR 1,009 total
includes taxes & fees
25 Oct - 26 Oct
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 Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Photo by © City of Chicago
Open Photo by © City 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.
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.
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.
