Find hotels in Sleepy Hollow, Chicago
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
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, (1,147 reviews)
"Fantastic stay"
Alan
The price is SAR 349
SAR 387 total
includes taxes & fees
10 Sep - 11 Sep
2. 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, (1,334 reviews)
"A great hotel in a bustling area. We had a great stay."
Joel
The price is SAR 927
SAR 1,103 total
includes taxes & fees
7 Sep - 8 Sep
3. Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHGWest Loop, 10.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,201 reviews)
"The hotel is so good."
Julenny
The price is SAR 605
SAR 764 total
includes taxes & fees
7 Sep - 8 Sep
4. 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, (2,590 reviews)
"Loved our stay"
Jaclyn
The price is SAR 725
SAR 862 total
includes taxes & fees
7 Sep - 8 Sep
5. LIVN - West Loop Chicago
LIVN - West Loop Chicago10.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (247 reviews)
"Great stay!"
Tomas
The price is SAR 453
SAR 532 total
includes taxes & fees
7 Sep - 8 Sep
6. The Emily Hotel
The Emily Hotel11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,339 reviews)
"Lovely property excellent location"
John
The price is SAR 895
SAR 1,064 total
includes taxes & fees
7 Sep - 8 Sep
7. The Hoxton, Chicago
The Hoxton, Chicago11.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,003 reviews)
"Great stay!"
Jordan
The price is SAR 973
SAR 1,267 total
includes taxes & fees
7 Sep - 8 Sep
8. 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, (1,002 reviews)
"Everything was fantastic and the staff went out of their way to be helpful and make sure we had a wonderful time!"
Amber
The price is SAR 935
SAR 1,112 total
includes taxes & fees
8 Sep - 9 Sep
9. The Buckingham Hotel
The Buckingham HotelThe Loop, 11.4 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,004 reviews)
"Beautiful hotel"
Ibrahim
The price is SAR 522
SAR 665 total
includes taxes & fees
7 Sep - 8 Sep
10. Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Central LoopThe Loop, 11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,409 reviews)
"Very clean, front desk staff were extremely friendly and welcoming. Beds were the most comfortable we have ever slept in when traveling!"
Theresa
The price is SAR 692
SAR 823 total
includes taxes & fees
7 Sep - 8 Sep
11. Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,730 reviews)
"The location of the hotel is great close to many things."
Melissa
The price is SAR 537
SAR 639 total
includes taxes & fees
7 Sep - 8 Sep
12. Level Chicago Fulton Market
Level Chicago Fulton MarketWest Loop, 11.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (561 reviews)
"Will stay here everytime in Chicago . Perfect location, units clean and well put together . Great amsninities."
Alex
The price is SAR 852
SAR 1,093 total
includes taxes & fees
8 Sep - 9 Sep
13. 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, (1,270 reviews)
"The staff were really nice and friendly. Our room was nice and clean. I would stay here again!"
Melanie
The price is SAR 681
SAR 810 total
includes taxes & fees
7 Sep - 8 Sep
14. 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, (2,910 reviews)
"Location, good stay"
Shilpa
The price is SAR 616
SAR 799 total
includes taxes & fees
7 Sep - 8 Sep
15. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio HotelTheatre District, 11.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,000 reviews)
"Great stay right in the Loop and convenient to the L."
Scott
The price is SAR 635
SAR 754 total
includes taxes & fees
6 Sep - 7 Sep
16. Le Méridien Essex Chicago
Le Méridien Essex ChicagoThe Loop, 11.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,008 reviews)
"This hotel was perfect. Room was a great size, clean, very friendly staff. Perfect for our work trip!"
amanda
The price is SAR 560
SAR 732 total
includes taxes & fees
7 Sep - 8 Sep
17. Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,135 reviews)
"Very nice place would stay again"
Konner
The price is SAR 635
SAR 865 total
includes taxes & fees
9 Sep - 10 Sep
18. 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, (2,447 reviews)
"Clean, friendly staff, quick valet, and a decent breakfast"
AMBER
The price is SAR 649
SAR 772 total
includes taxes & fees
7 Sep - 8 Sep
19. 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, (1,580 reviews)
"Great place to stay!"
LISA
The price is SAR 747
SAR 888 total
includes taxes & fees
7 Sep - 8 Sep
20. 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, (2,147 reviews)
"Great stay"
Dhannetta
The price is SAR 603
SAR 717 total
includes taxes & fees
10 Sep - 11 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 Navy Pier and Michigan Avenue 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.
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.
Top Sleepy Hollow Hotel Reviews
InterContinental Chicago Magnificent Mile by IHG
10/10 Excellent
