Find hotels in Sleepy Hollow, Chicago from ₩45,860

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Jul 14 - Jul 15
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Jul 18 - Jul 20
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Discover 4,674 Sleepy Hollow hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

The Chicago Hotel Collection Ambassador Gold Coast
Terrace/patio

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very Good, (1030)
"Great Front desk staff! All staff was very friendly and location was wonderful 😀"
The price is ₩50,955
₩253,720 total
includes taxes & fees
Jul 15 - Jul 16
The Chicago Hotel Collection Ambassador Gold Coast
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1257)
"Comfy bed and linens, nice amenities and the staff checked on me via text throughout the stay. "
The price is ₩124,550
₩186,628 total
includes taxes & fees
Aug 10 - Aug 11
Claridge House
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2061)
"Amazing property clean comfy bedding and wonderful views"
The price is ₩314,888
₩409,584 total
includes taxes & fees
Jul 27 - Jul 28
Sable at Navy Pier Chicago, Curio Collection by Hilton
The Chicago Hotel Collection - Magnificent Mile
Breakfast and dinner served

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1101)
"We enjoyed our time at this stay. "
The price is ₩45,860
₩247,739 total
includes taxes & fees
Jul 27 - Jul 28
The Chicago Hotel Collection - Magnificent Mile
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2067)
"Stayed many times, great fun!"
The price is ₩153,691
₩204,667 total
includes taxes & fees
Aug 6 - Aug 7
Freehand Chicago
Millennium Knickerbocker Chicago
Lobby

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1882)
"Great location near bars and restaurants "
The price is ₩174,899
₩237,650 total
includes taxes & fees
Aug 13 - Aug 14
Millennium Knickerbocker Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1014)
"Great parking!"
The price is ₩172,111
₩202,042 total
includes taxes & fees
Jul 27 - Jul 28
Best Western River North Hotel
Hilton Chicago/Magnificent Mile Suites
Restaurant

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2440)
"Friendly staff, beautiful views, excellent location "
The price is ₩207,194
₩243,224 total
includes taxes & fees
Aug 10 - Aug 11
Hilton Chicago/Magnificent Mile Suites
Holiday Inn Express Chicago - Magnificent Mile by IHG
Exterior

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very Good, (1008)
"Excellent area of Chicago with dining and shopping "
The price is ₩208,227
₩244,433 total
includes taxes & fees
Aug 7 - Aug 8
Holiday Inn Express Chicago - Magnificent Mile by IHG
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (514)
"The rooms were excellent"
The price is ₩92,958
₩222,173 total
includes taxes & fees
Jul 16 - Jul 17
The Chicago Hotel Collection River North
Ohio House Motel
Reception

Ohio House Motel

2.5 star property
9.0 out of 10, Wonderful, (1018)
"Great place to stay!"
Ohio House Motel
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1678)
"Great stay"
The price is ₩205,541
₩254,492 total
includes taxes & fees
Jul 27 - Jul 28
Hotel Saint Clair- Magnificent Mile
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2238)
"Great value for the cost. Pleasant room and facilities, and very friendly and helpful staff. Will stay there again. "
The price is ₩174,762
₩205,155 total
includes taxes & fees
Aug 4 - Aug 5
Travelodge by Wyndham Downtown Chicago
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3037)
"Loved our stay! "
The price is ₩198,311
₩232,797 total
includes taxes & fees
Jul 24 - Jul 25
Eurostars Magnificent Mile
LondonHouse Chicago, Curio Collection by Hilton
Lobby

LondonHouse Chicago, Curio Collection by Hilton

4.5 star property
9.4 out of 10, Exceptional, (3341)
"Great stay"
The price is ₩235,288
₩276,205 total
includes taxes & fees
Aug 10 - Aug 11
LondonHouse Chicago, Curio Collection by Hilton
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very Good, (1898)
"Great stay! "
The price is ₩188,395
₩221,157 total
includes taxes & fees
Aug 10 - Aug 11
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very Good, (122)
"Good hotel "
The price is ₩181,854
₩213,478 total
includes taxes & fees
Aug 6 - Aug 7
FOUND Hotel Chicago River North
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8961)
"Great location, beautiful hotel "
The price is ₩203,578
₩238,981 total
includes taxes & fees
Aug 5 - Aug 6
Congress Plaza Hotel
The Godfrey Hotel Chicago
American cuisine, alfresco dining

The Godfrey Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1891)
"Great hotel in a great location. Would definitely stay again "
The price is ₩232,740
₩305,548 total
includes taxes & fees
Jul 27 - Jul 28
The Godfrey Hotel Chicago
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very Good, (3531)
"Very pleasant place to stay "
The price is ₩249,335
₩292,694 total
includes taxes & fees
Aug 10 - Aug 11
Hilton Garden Inn Chicago Downtown/Magnificent Mile
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 showing a city
Downtown Chicago map

Downtown Chicago

5 out of top 10 points of interest in this area

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 - River North
Magnificent Mile map

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 - Downtown which includes a river or creek
The Loop map

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 showing railway items, street scenes and a city
River North map

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.

Chicago which includes modern architecture and a city
Lincoln Park map

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.

Frequently asked questions

What's it like in Sleepy Hollow?

Sleepy Hollow is a neighborhood that travelers like for its restaurants.

If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?

Yes! The majority of hotel room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals available in Sleepy Hollow.

Where can I learn more about changing or cancelling my trip to Sleepy Hollow?

For more information about picking new dates or cancelling your trip to Sleepy Hollow, click here.

What can I see and do in this Chicago neighborhood?

Places you might want to visit in the area around Sleepy Hollow include Hawthorne Works Museum and Balzekas Museum of Lithuanian Culture. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.