Find hotels in Sleepy Hollow, Chicago from NT$3,107

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Aug 29 - Aug 30
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Aug 30 - Aug 31
This weekend
Aug 29 - Aug 31
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Sep 5 - Sep 7

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Discover 4,907 Sleepy Hollow hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

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, (2109)
"Great place to stay!"
The price is NT$5,715
NT$7,595 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2252)
"Great stay "
The price is NT$3,107
NT$4,186 total
includes taxes & fees
Sep 2 - Sep 3
Freehand Chicago
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1341)
"Great stay highly recommend!! "
Claridge House
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1008)
"Great place to stay!"
The price is NT$3,361
NT$3,945 total
includes taxes & fees
Sep 2 - Sep 3
Ohio House Motel
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2617)
"Great hotel! "
The price is NT$3,091
NT$3,628 total
includes taxes & fees
Sep 2 - Sep 3
Best Western Grant Park Hotel
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1703)
"Had a great stay! The area is very walkable and convenient!!"
Hotel Saint Clair- Magnificent Mile
The Godfrey Hotel Chicago
American cuisine, alfresco dining

The Godfrey Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1907)
"Good location and great rooftop"
The price is NT$5,164
NT$6,779 total
includes taxes & fees
Sep 1 - Sep 2
The Godfrey Hotel Chicago
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1012)
"Great location and hotel "
The price is NT$4,129
NT$4,847 total
includes taxes & fees
Sep 3 - Sep 4
Ivy Boutique Hotel
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very Good, (213)
"Great place "
The price is NT$3,135
NT$3,680 total
includes taxes & fees
Sep 2 - Sep 3
FOUND Hotel Chicago River North
Hotel Felix River North/Magnificent Mile
Lobby sitting area

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (2102)
"Great spot, good location, nice rooms. "
Hotel Felix River North/Magnificent Mile
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1829)
"Amazing place to stay"
The price is NT$3,941
NT$4,627 total
includes taxes & fees
Sep 1 - Sep 2
Central Loop Hotel
Club Quarters Hotel, Central Loop, Chicago
Breakfast, lunch and dinner served

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3366)
"Great location, quiet rooms "
The price is NT$3,941
NT$4,627 total
includes taxes & fees
Sep 1 - Sep 2
Club Quarters Hotel, Central Loop, Chicago
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1039)
"Its a really nice place ,very pleased. "
The price is NT$3,610
NT$4,238 total
includes taxes & fees
Sep 2 - Sep 3
Best Western River North Hotel
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (575)
"It was a wonderful place to stay! "
The price is NT$3,890
NT$4,566 total
includes taxes & fees
Sep 1 - Sep 2
The Chicago Hotel Collection River North
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2322)
"I had a very good stay 10 out of 10 recommend"
The price is NT$2,997
NT$3,518 total
includes taxes & fees
Sep 2 - Sep 3
Travelodge by Wyndham Downtown Chicago
River Hotel
Lobby

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4590)
"Great place to stay, staff was very friendly"
The price is NT$4,553
NT$5,344 total
includes taxes & fees
Sep 2 - Sep 3
River Hotel
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1963)
"Great stay"
The price is NT$4,155
NT$5,595 total
includes taxes & fees
Sep 2 - Sep 3
Millennium Knickerbocker Chicago
The Chicago Hotel Collection - Magnificent Mile
Rooftop terrace

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1209)
"Great location, nice room and roomy bathroom and good breakfast."
The Chicago Hotel Collection - Magnificent Mile
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2810)
"Close to everything, easy check-in/out and friendly staff!"
The price is NT$3,941
NT$4,627 total
includes taxes & fees
Sep 2 - Sep 3
Aloft Chicago Mag Mile
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9056)
"Family had a great stay. "
The price is NT$6,030
NT$7,078 total
includes taxes & fees
Sep 15 - Sep 16
Congress Plaza Hotel
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

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

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

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

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

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

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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.