
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, (2,433 reviews)
The price is CA $258
CA $350 total
includes taxes & fees
Apr 6 - Apr 7

Aloft Chicago Mag Mile
Aloft Chicago Mag MileStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,156 reviews)
The price is CA $166
CA $194 total
includes taxes & fees
Apr 6 - Apr 7

River Hotel
River HotelThe Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,049 reviews)
The price is CA $152
CA $178 total
includes taxes & fees
Apr 5 - Apr 6

Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,715 reviews)
The price is CA $291
CA $382 total
includes taxes & fees
Apr 10 - Apr 11

Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,235 reviews)
The price is CA $162
CA $233 total
includes taxes & fees
Apr 9 - Apr 10

Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,007 reviews)
The price is CA $150
CA $177 total
includes taxes & fees
Apr 5 - Apr 6

Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium ParkThe Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,097 reviews)
The price is CA $277
CA $374 total
includes taxes & fees
Apr 5 - Apr 6

Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,711 reviews)
The price is CA $180
CA $250 total
includes taxes & fees
Apr 28 - Apr 29

Central Loop Hotel
Central Loop HotelTheatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,056 reviews)
The price is CA $129
CA $151 total
includes taxes & fees
Apr 6 - Apr 7

Hyatt Regency Chicago
Hyatt Regency ChicagoThe Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,473 reviews)
The price is CA $278
CA $376 total
includes taxes & fees
Apr 5 - Apr 6

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, (1,305 reviews)
The price is CA $216
CA $254 total
includes taxes & fees
Apr 5 - Apr 6

Swissotel - Chicago
Swissotel - Chicago13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,232 reviews)
The price is CA $299
CA $401 total
includes taxes & fees
Apr 10 - Apr 11

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, (2,148 reviews)
The price is CA $151
CA $178 total
includes taxes & fees
Apr 6 - Apr 7

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,039 reviews)
The price is CA $180
CA $211 total
includes taxes & fees
Apr 5 - Apr 6

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, (1,343 reviews)
The price is CA $190
CA $223 total
includes taxes & fees
Apr 5 - Apr 6

Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,365 reviews)
The price is CA $249
CA $334 total
includes taxes & fees
Apr 5 - Apr 6

DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,393 reviews)
The price is CA $166
CA $194 total
includes taxes & fees
Apr 5 - Apr 6

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio HotelTheatre District, 11.6 km from Sleepy Hollow
8.2 out of 10, Very good, (1,004 reviews)
The price is CA $207
CA $243 total
includes taxes & fees
Apr 4 - Apr 5

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, (3,416 reviews)
The price is CA $145
CA $170 total
includes taxes & fees
Apr 27 - Apr 28

FOUND Hotel Chicago River North
FOUND Hotel Chicago River NorthRiver North, 12.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (525 reviews)
The price is CA $115
CA $135 total
includes taxes & fees
Apr 5 - Apr 6
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.

O'Hare
Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.

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.
Top Sleepy Hollow Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North
4/10 Poor
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