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, (1,152 reviews)
"Fantastic stay"
Alan
The price is SAR 414
SAR 459 total
includes taxes & fees
22 Sep - 23 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, (1,323 reviews)
"Good place to stay"
Patrick
The price is SAR 819
SAR 973 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, (1,187 reviews)
"The hotel is so good."
Julenny
The price is SAR 559
SAR 710 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, (2,557 reviews)
"Loved our stay"
Jaclyn
The price is SAR 648
SAR 770 total
includes taxes & fees
30 Aug - 31 Aug
5. LIVN - West Loop Chicago
LIVN - West Loop Chicago10.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (233 reviews)
"The place located nicely and rooms are nice"
patrick
The price is SAR 541
SAR 635 total
includes taxes & fees
30 Aug - 31 Aug
6. The Emily Hotel
The Emily Hotel11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,336 reviews)
"Lovely property excellent location"
John
The price is SAR 1,044
SAR 1,242 total
includes taxes & fees
30 Aug - 31 Aug
7. 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)
"Great location"
Carmen
The price is SAR 889
SAR 1,057 total
includes taxes & fees
31 Aug - 1 Sep
8. The Buckingham Hotel
The Buckingham HotelThe Loop, 11.4 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,002 reviews)
"Nice place to stay"
Dominique
The price is SAR 591
SAR 747 total
includes taxes & fees
30 Aug - 31 Aug
9. 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, (1,415 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 594
SAR 706 total
includes taxes & fees
7 Sep - 8 Sep
10. Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,736 reviews)
"Very good hotel"
Diego
The price is SAR 524
SAR 623 total
includes taxes & fees
1 Sep - 2 Sep
11. Level Chicago Fulton Market
Level Chicago Fulton MarketWest Loop, 11.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (557 reviews)
"Will stay here everytime in Chicago . Perfect location, units clean and well put together . Great amsninities."
Alex
The price is SAR 719
SAR 937 total
includes taxes & fees
30 Aug - 31 Aug
12. 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, (1,273 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
30 Aug - 31 Aug
13. 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, (2,884 reviews)
"Location, good stay"
Shilpa
The price is SAR 470
SAR 625 total
includes taxes & fees
30 Aug - 31 Aug
14. 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)
"It was a super place to stay!!! Great location!!!"
Victoria
The price is SAR 597
SAR 710 total
includes taxes & fees
30 Aug - 31 Aug
15. Le Méridien Essex Chicago
Le Méridien Essex ChicagoThe Loop, 11.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,000 reviews)
"The room, the staff and the restaurant were all great!"
Jesse
The price is SAR 635
SAR 821 total
includes taxes & fees
30 Aug - 31 Aug
16. Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,074 reviews)
"Very nice place would stay again"
Konner
The price is SAR 699
SAR 941 total
includes taxes & fees
9 Sep - 10 Sep
17. 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, (2,435 reviews)
"Clean, friendly staff, quick valet, and a decent breakfast"
AMBER
The price is SAR 603
SAR 717 total
includes taxes & fees
7 Sep - 8 Sep
18. 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, (1,556 reviews)
"Great place to stay!"
LISA
The price is SAR 635
SAR 754 total
includes taxes & fees
7 Sep - 8 Sep
19. 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, (2,132 reviews)
"Great stay"
Dhannetta
The price is SAR 587
SAR 698 total
includes taxes & fees
7 Sep - 8 Sep
20. Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, ChicagoTheatre District, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (3,644 reviews)
"Greta stay and location"
Youssef
The price is SAR 536
SAR 637 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 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.
