Find hotels in Sleepy Hollow, Chicago
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Discover Sleepy Hollow hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.
DoubleTree by Hilton Chicago - Magnificent Mile
Streeterville, 8.3 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2173)
"Great stay "
Melinda
$98 nightly
The price is $115
Dec 7 - Dec 8
Total with taxes and fees
River Hotel
The Loop, 7.9 mi from Sleepy Hollow
8.8 out of 10, Excellent, (4857)
"Front desk is amazing, rooms are clean and great location"
Glen
$92 nightly
The price is $108
Dec 7 - Dec 8
Total with taxes and fees
Eurostars Magnificent Mile
River North, 8.1 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (3147)
"Location was great "
Hamik
$106 nightly
The price is $125
Dec 4 - Dec 5
Total with taxes and fees
Hilton Chicago
The Loop, 7.3 mi from Sleepy Hollow
8.4 out of 10, Very Good, (2334)
"Clean Rooms & very nice staff"
Teresa
$131 nightly
The price is $154
Dec 20 - Dec 21
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
Streeterville, 8.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2261)
"Room was spotless…staff was great!"
Tamika
$122 nightly
The price is $143
Dec 16 - Dec 17
Total with taxes and fees
Aloft Chicago Mag Mile
Streeterville, 8.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2950)
"Great location!!"
sarah e
$90 nightly
The price is $106
Dec 7 - Dec 8
Total with taxes and fees
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. Learn more about Sleepy Hollow
Learn more about Sleepy Hollow
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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