Find hotels in Sleepy Hollow, Chicago
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Our top choices for Sleepy Hollow hotels
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, (2,478 reviews)
"Great place to stay "
Mark
The price is ₩285,764
₩389,999 total
includes taxes & fees
May 26 - May 27
Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,417 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
Cynthia
The price is ₩218,083
₩296,174 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,239 reviews)
"Super nice staff, nice room, great location. We really enjoyed our stay. "
Jim
The price is ₩175,837
₩254,069 total
includes taxes & fees
May 25 - May 26
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,991 reviews)
"Enjoyed the stay"
Adam
The price is ₩195,870
₩274,436 total
includes taxes & fees
May 25 - May 26
River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,143 reviews)
"Very convenient location, kind staff, and comfy rooms. "
Molly Christina
The price is ₩190,214
₩223,306 total
includes taxes & fees
Apr 30 - May 1
Arlo Chicago
Arlo ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,101 reviews)
"Great location! Loved staying here"
Nicole
The price is ₩295,992
₩395,940 total
includes taxes & fees
May 24 - May 25
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, (1,967 reviews)
"Easy check in and clean rooms, comfortable beds and easy access to everything downtown."
Megan
The price is ₩193,016
₩229,496 total
includes taxes & fees
May 26 - May 27
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopTheatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,054 reviews)
"Wonderful restaurant, amazing food."
Robert
The price is ₩196,115
₩276,364 total
includes taxes & fees
May 25 - May 26
FOUND Hotel Chicago River North
FOUND Hotel Chicago River NorthRiver North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very Good, (573 reviews)
"Great location great staff great hotel!"
Refak
The price is ₩138,016
₩162,017 total
includes taxes & fees
Apr 29 - Apr 30
Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (10,160 reviews)
"Great stay"
Matthew
The price is ₩196,761
₩233,934 total
includes taxes & fees
May 8 - May 9
Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,685 reviews)
"Great location, right across the street from the park."
Jamison
The price is ₩190,214
₩226,158 total
includes taxes & fees
May 26 - May 27
Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,759 reviews)
"Clean room and great location "
Diana
The price is ₩234,450
₩322,051 total
includes taxes & fees
May 25 - May 26
The Chicago Hotel Collection Ambassador Gold Coast
The Chicago Hotel Collection Ambassador Gold CoastGold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very Good, (1,394 reviews)
"Great stay, love the surrounding area. Rooms a bit small but overall a great stay. "
Eric
The price is ₩266,776
₩317,188 total
includes taxes & fees
May 26 - May 27
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio HotelTheatre District, 11.6 km from Sleepy Hollow
8.4 out of 10, Very Good, (1,011 reviews)
"A fantastic hotel for solo travelers - perfect area, close to museums and restaurants, great bar"
Michelle Renee
The price is ₩199,062
₩236,678 total
includes taxes & fees
May 25 - May 26
Club Quarters Hotel Wacker at Michigan, Chicago
Club Quarters Hotel Wacker at Michigan, ChicagoThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,228 reviews)
"Perfect location great room for the price "
Lisa
The price is ₩190,214
₩223,306 total
includes taxes & fees
Apr 30 - May 1
Freehand Chicago
Freehand ChicagoRiver North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (2,922 reviews)
"Great stay"
Agnes Nmabila
The price is ₩147,306
₩201,421 total
includes taxes & fees
May 25 - May 26
Central Loop Hotel
Central Loop HotelTheatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,104 reviews)
"Nice hotel perfect location "
YOEL
The price is ₩190,214
₩226,158 total
includes taxes & fees
May 25 - May 26
Hotel Saint Clair- Magnificent Mile
Hotel Saint Clair- Magnificent MileStreeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very Good, (1,892 reviews)
"Location Good"
Lisa
The price is ₩143,722
₩171,605 total
includes taxes & fees
Apr 29 - Apr 30
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,141 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
Nicole
The price is ₩253,914
₩353,829 total
includes taxes & fees
May 8 - May 9
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection HotelThe Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,234 reviews)
"Really nice stay. "
Rachael Lindsay
The price is ₩222,949
₩261,720 total
includes taxes & fees
May 25 - May 26
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
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
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
Palmer House a Hilton Hotel
10/10 Excellent
