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. 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, (2,697 reviews)
"Amazing place to stay"
Shanequa
The price is SAR 1,073
SAR 1,405 total
includes taxes & fees
1 Oct - 2 Oct
3. Sheraton Grand Chicago Riverwalk
Sheraton Grand Chicago RiverwalkStreeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,827 reviews)
"Quick check in process, great location, helpful staff"
Brandi
The price is SAR 1,198
SAR 1,559 total
includes taxes & fees
25 Sep - 26 Sep
4. Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,504 reviews)
"Location was great and rooms were clean"
Aagrim
The price is SAR 879
SAR 1,178 total
includes taxes & fees
27 Sep - 28 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, (2,574 reviews)
"Great location!"
Madelyn
The price is SAR 827
SAR 983 total
includes taxes & fees
27 Sep - 28 Sep
6. Hilton Grand Vacations Club Chicago Magnificent Mile
Hilton Grand Vacations Club Chicago Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (468 reviews)
"Very nice clean and comfortable perfect stay"
Shaniyah
The price is SAR 890
SAR 1,058 total
includes taxes & fees
30 Sep - 1 Oct
7. Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very good, (3,014 reviews)
"The hotel was a great location, so many things to do in a walkable distance"
Valerie
The price is SAR 895
SAR 1,174 total
includes taxes & fees
20 Sep - 21 Sep
8. Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,109 reviews)
"Good place to stay"
Mia
The price is SAR 1,174
SAR 1,512 total
includes taxes & fees
20 Sep - 21 Sep
9. Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,301 reviews)
"Excellent stay as always."
Amit
The price is SAR 1,102
SAR 1,444 total
includes taxes & fees
20 Sep - 21 Sep
10. 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 769
SAR 914 total
includes taxes & fees
27 Sep - 28 Sep
11. Ivy Boutique Hotel
Ivy Boutique HotelStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,452 reviews)
"Great area plenty to do and hotel room was amazing but a bit pricey"
Eduardo
The price is SAR 833
SAR 978 total
includes taxes & fees
27 Sep - 28 Sep
12. 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, (2,663 reviews)
"Very friendly and helpfull staff, clean rooms, great location plus breakfast equals an amazing stay!"
Kelly
The price is SAR 724
SAR 861 total
includes taxes & fees
30 Sep - 1 Oct
13. 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)
"Loved this hotel, friendly staff and such a great spot in the city!"
Marissa
The price is SAR 710
SAR 844 total
includes taxes & fees
20 Sep - 21 Sep
14. Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,930 reviews)
"Very nice hotel, friendly staff, good location"
Brian
The price is SAR 763
SAR 907 total
includes taxes & fees
27 Sep - 28 Sep
15. Millennium Hotel Knickerbocker Chicago
Millennium Hotel Knickerbocker ChicagoStreeterville, 13.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,940 reviews)
"Nice place to stay"
Vijay
The price is SAR 575
SAR 773 total
includes taxes & fees
21 Sep - 22 Sep
16. Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,460 reviews)
"Great place to stay when available and reasonably priced."
Jerry
The price is SAR 1,258
SAR 1,630 total
includes taxes & fees
2 Oct - 3 Oct
17. Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,125 reviews)
"Excellent Location, friendly staff."
zhuo
The price is SAR 796
SAR 1,058 total
includes taxes & fees
27 Sep - 28 Sep
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, (2,180 reviews)
"The hotel was well located and beautiful."
Patricia
The price is SAR 530
SAR 630 total
includes taxes & fees
20 Sep - 21 Sep
19. Hotel Saint Clair- Magnificent Mile
Hotel Saint Clair- Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,224 reviews)
"Nice place to stay"
Caleb
The price is SAR 561
SAR 678 total
includes taxes & fees
20 Sep - 21 Sep
20. Hampton Inn Chicago Downtown/Magnificent Mile
Hampton Inn Chicago Downtown/Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
8.0 out of 10, Very good, (1,614 reviews)
"Nice clean rooms and a perfect breakfast."
Kevin
The price is SAR 731
SAR 869 total
includes taxes & fees
27 Sep - 28 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.
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.
Top Sleepy Hollow Hotel Reviews
The Royal Sonesta Chicago Downtown
10/10 Excellent
