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Aug 14 - Aug 15
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Aug 15 - Aug 16
This weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24

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Discover 4,783 Sleepy Hollow hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

River Hotel
Lobby

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4510)
"Great stay and great location"
The price is NT$3,281
NT$3,851 total
includes taxes & fees
Sep 1 - Sep 2
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, sun loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1982)
"Pool area and deck were great for the family, beds were comfortable, location is great."
The price is NT$4,767
NT$5,596 total
includes taxes & fees
Aug 24 - Aug 25
DoubleTree by Hilton Chicago - Magnificent Mile
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, (2068)
"Best hotel "
The price is NT$4,886
NT$6,604 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3063)
"Great stay!"
The price is NT$4,791
NT$5,624 total
includes taxes & fees
Sep 1 - Sep 2
Eurostars Magnificent Mile
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2077)
"Good hotel in good location. "
The price is NT$4,190
NT$5,797 total
includes taxes & fees
Sep 2 - Sep 3
Hilton Chicago
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8908)
"Great place to stay."
The price is NT$5,632
NT$6,612 total
includes taxes & fees
Sep 14 - Sep 15
Congress Plaza Hotel
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1028)
"Great location "
The price is NT$3,792
NT$4,452 total
includes taxes & fees
Aug 24 - Aug 25
Best Western River North Hotel
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, (3678)
"Ideally located with great shopping and dining experiences nearby."
The price is NT$4,301
NT$5,050 total
includes taxes & fees
Sep 4 - Sep 5
Hilton Garden Inn Chicago Downtown/Magnificent Mile
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3563)
"Great hotel"
The price is NT$4,047
NT$4,750 total
includes taxes & fees
Sep 1 - Sep 2
citizenM Chicago Downtown
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2792)
"We love our stay here !"
The price is NT$4,162
NT$4,886 total
includes taxes & fees
Sep 1 - Sep 2
Aloft Chicago Mag Mile
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
8.8 out of 10, Excellent, (1371)
"Staff was so friendly and the rooms were really clean!"
The price is NT$3,983
NT$4,675 total
includes taxes & fees
Aug 24 - Aug 25
Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very Good, (1005)
"Friendly staff and close to the places I wanted to go to "
The price is NT$4,432
NT$5,562 total
includes taxes & fees
Sep 3 - Sep 4
Holiday Inn & Suites Chicago - Downtown by IHG
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2198)
"Good spot when staying for lolla "
The price is NT$3,153
NT$4,229 total
includes taxes & fees
Aug 26 - Aug 27
Freehand Chicago
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2625)
"Great location and hotel!"
The price is NT$4,301
NT$5,049 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (548)
"It was a wonderful place to stay! "
The price is NT$3,812
NT$4,475 total
includes taxes & fees
Aug 18 - Aug 19
The Chicago Hotel Collection River North
The Whitehall Hotel, BW Premier Collection
1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very Good, (3519)
"Excellent location, renovated rooms, easy access and near attractions"
The price is NT$3,451
NT$4,051 total
includes taxes & fees
Sep 2 - Sep 3
The Whitehall Hotel, BW Premier Collection
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very Good, (1858)
"Nice place to stay"
The price is NT$5,192
NT$6,844 total
includes taxes & fees
Sep 2 - Sep 3
Palmer House a Hilton Hotel
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2469)
"Had a wonderful stay here and staff was super friendly!"
The price is NT$4,015
NT$5,241 total
includes taxes & fees
Sep 1 - Sep 2
La Quinta Inn & Suites by Wyndham Chicago Downtown
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1935)
"Very nice and comfortable stay"
Silversmith Hotel Chicago Downtown
Thompson Chicago, by Hyatt
Restaurant

Thompson Chicago, by Hyatt

4.5 star property
9.0 out of 10, Wonderful, (1195)
"Perfect location, great staff and comfortable bed"
The price is NT$5,001
NT$6,754 total
includes taxes & fees
Sep 1 - Sep 2
Thompson Chicago, by Hyatt
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.
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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.

Top Sleepy Hollow Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"
Emily 3-night trip
Posted 12 hours ago
Congress Plaza Hotel

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.