
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, (2,404 reviews)
The price is CA $198
CA $280 total
includes taxes & fees
Mar 24 - Mar 25

Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,685 reviews)
The price is CA $179
CA $250 total
includes taxes & fees
Apr 1 - Apr 2

Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (9,948 reviews)
The price is CA $133
CA $156 total
includes taxes & fees
Apr 1 - Apr 2

River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,042 reviews)
The price is CA $130
CA $152 total
includes taxes & fees
Mar 23 - Mar 24

Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,231 reviews)
The price is CA $167
CA $244 total
includes taxes & fees
Mar 29 - Mar 30

Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,695 reviews)
The price is CA $131
CA $153 total
includes taxes & fees
Mar 24 - Mar 25

Central Loop Hotel
Central Loop HotelTheatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,035 reviews)
The price is CA $134
CA $157 total
includes taxes & fees
Mar 29 - Mar 30

Arlo Chicago
Arlo ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,022 reviews)
The price is CA $172
CA $242 total
includes taxes & fees
Mar 24 - Mar 25

FOUND Hotel Chicago River North
FOUND Hotel Chicago River NorthRiver North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very good, (496 reviews)
The price is CA $116
CA $136 total
includes taxes & fees
Mar 24 - Mar 25

L7 Chicago by LOTTE
L7 Chicago by LOTTETheatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (3,779 reviews)
The price is CA $210
CA $247 total
includes taxes & fees
Mar 24 - Mar 25

Freehand Chicago
Freehand ChicagoRiver North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,804 reviews)
The price is CA $94
CA $135 total
includes taxes & fees
Mar 30 - Mar 31

Palmer House a Hilton Hotel
Palmer House a Hilton HotelTheatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,328 reviews)
The price is CA $184
CA $251 total
includes taxes & fees
Apr 5 - Apr 6

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, (1,910 reviews)
The price is CA $162
CA $190 total
includes taxes & fees
Apr 13 - Apr 14

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, (2,122 reviews)
The price is CA $130
CA $152 total
includes taxes & fees
Mar 19 - Mar 20

Aloft Chicago Mag Mile
Aloft Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,147 reviews)
The price is CA $148
CA $174 total
includes taxes & fees
Mar 22 - Mar 23

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, (1,314 reviews)
The price is CA $165
CA $194 total
includes taxes & fees
Mar 23 - Mar 24

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, (3,421 reviews)
The price is CA $132
CA $155 total
includes taxes & fees
Mar 31 - Apr 1

Le Méridien Essex Chicago
Le Méridien Essex ChicagoThe Loop, 11.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,008 reviews)
The price is CA $133
CA $180 total
includes taxes & fees
Apr 12 - Apr 13

The Chicago Hotel Collection - Magnificent Mile
The Chicago Hotel Collection - Magnificent MileStreeterville, 13.5 km from Sleepy Hollow
7.6 out of 10, Good, (1,237 reviews)
The price is CA $165
CA $194 total
includes taxes & fees
Mar 18 - Mar 19
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

Fairmont Chicago at Millennium Park
2/10 Terrible
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