
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, (2,482 reviews)
The price is CA $249
CA $343 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, (2,770 reviews)
The price is CA $216
CA $297 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, (4,034 reviews)
The price is CA $183
CA $256 total
includes taxes & fees
May 27 - May 28

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, (1,976 reviews)
The price is CA $178
CA $212 total
includes taxes & fees
May 26 - May 27

L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (4,002 reviews)
The price is CA $196
CA $234 total
includes taxes & fees
May 25 - May 26

Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,134 reviews)
The price is CA $170
CA $202 total
includes taxes & fees
May 8 - May 9

Freehand Chicago
Freehand ChicagoRiver North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,939 reviews)
The price is CA $133
CA $182 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, (2,244 reviews)
The price is CA $162
CA $234 total
includes taxes & fees
May 25 - May 26

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, (1,056 reviews)
The price is CA $181
CA $255 total
includes taxes & fees
May 25 - May 26

Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,296 reviews)
The price is CA $269
CA $368 total
includes taxes & fees
May 27 - May 28

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, (3,682 reviews)
The price is CA $245
CA $331 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, (2,428 reviews)
The price is CA $201
CA $279 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, (580 reviews)
The price is CA $121
CA $142 total
includes taxes & fees
May 26 - May 27

Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoThe Loop, 11.8 km from Sleepy Hollow
7.4 out of 10, Good, (2,574 reviews)
The price is CA $143
CA $170 total
includes taxes & fees
May 27 - May 28

River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,156 reviews)
The price is CA $184
CA $218 total
includes taxes & fees
May 26 - May 27

Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,688 reviews)
The price is CA $158
CA $188 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)
The price is CA $127
CA $150 total
includes taxes & fees
May 25 - May 26

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, (1,007 reviews)
The price is CA $202
CA $241 total
includes taxes & fees
May 8 - May 9

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent MileStreeterville, 13.5 km from Sleepy Hollow
7.8 out of 10, Good, (1,363 reviews)
The price is CA $168
CA $200 total
includes taxes & fees
May 9 - May 10

Aloft Chicago Mag Mile
Aloft Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,218 reviews)
The price is CA $202
CA $241 total
includes taxes & fees
May 10 - May 11
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.
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