
Hotels in Sleepy Hollow, Chicago
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Our top choices for Sleepy Hollow hotels

The Godfrey Hotel Chicago
The Godfrey Hotel ChicagoRiver North, 12.8 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,296 reviews)
The price is CA $188
CA $255 total
includes taxes & fees
Jul 1 - Jul 2

Holiday Inn Chicago Dwtn - The Mart by IHG
Holiday Inn Chicago Dwtn - The Mart by IHGRiver North, 11.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,404 reviews)
The price is CA $249
CA $296 total
includes taxes & fees
Jul 1 - Jul 2

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, (1,445 reviews)
The price is CA $308
CA $366 total
includes taxes & fees
Jul 1 - Jul 2

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
Homewood Suites by Hilton Chicago Downtown/Magnificent MileStreeterville, 13.4 km from Sleepy Hollow
8.2 out of 10, Very good, (1,009 reviews)
The price is CA $276
CA $328 total
includes taxes & fees
Jul 2 - Jul 3

Arlo Chicago
Arlo ChicagoTheatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,122 reviews)
The price is CA $279
CA $374 total
includes taxes & fees
Jul 5 - Jul 6

Congress Plaza Hotel
Congress Plaza HotelThe Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,295 reviews)
The price is CA $191
CA $227 total
includes taxes & fees
Jun 29 - Jun 30

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesStreeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,437 reviews)
The price is CA $195
CA $232 total
includes taxes & fees
Jul 1 - Jul 2

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, (1,607 reviews)
The price is CA $215
CA $256 total
includes taxes & fees
Jul 1 - Jul 2

Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown ChicagoThe Loop, 11.8 km from Sleepy Hollow
7.6 out of 10, Good, (2,601 reviews)
The price is CA $177
CA $211 total
includes taxes & fees
Jul 5 - Jul 6

Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoStreeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,471 reviews)
The price is CA $224
CA $306 total
includes taxes & fees
Jul 5 - Jul 6

Omni Chicago Hotel
Omni Chicago HotelStreeterville, 13.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,814 reviews)
The price is CA $214
CA $301 total
includes taxes & fees
Jul 5 - Jul 6

Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago DowntownTheatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,254 reviews)
The price is CA $171
CA $246 total
includes taxes & fees
Jul 5 - Jul 6

Hotel 55 Chicago Downtown
Hotel 55 Chicago DowntownRiver North, 13.1 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,570 reviews)
The price is CA $197
CA $276 total
includes taxes & fees
Jul 1 - Jul 2

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, (1,250 reviews)
The price is CA $237
CA $281 total
includes taxes & fees
Jul 5 - Jul 6

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, (3,738 reviews)
The price is CA $332
CA $435 total
includes taxes & fees
Jul 1 - Jul 2

Best Western Grant Park Hotel
Best Western Grant Park HotelThe Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,710 reviews)
The price is CA $167
CA $198 total
includes taxes & fees
Jul 1 - Jul 2

Hilton Chicago
Hilton ChicagoThe Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,863 reviews)
The price is CA $274
CA $367 total
includes taxes & fees
Jul 1 - Jul 2

Warwick Allerton - Chicago
Warwick Allerton - ChicagoStreeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,008 reviews)
The price is CA $164
CA $236 total
includes taxes & fees
Jul 2 - Jul 3

The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier CollectionStreeterville, 13.5 km from Sleepy Hollow
8.4 out of 10, Very good, (3,927 reviews)
The price is CA $189
CA $225 total
includes taxes & fees
Jun 30 - Jul 1

Freehand Chicago
Freehand ChicagoRiver North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (3,128 reviews)
The price is CA $167
CA $265 total
includes taxes & fees
Jul 5 - Jul 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.

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

Travelodge by Wyndham Downtown Chicago
10/10 Excellent
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