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Jul 24 - Jul 25
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Jul 25 - Jul 26
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Jul 25 - Jul 27
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Aug 1 - Aug 3

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Discover 4,749 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
Relax in style with lounge chairs and bar stools amidst a scenic backdrop.

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2053)
"Beautiful property, will definitely stay there again."
The price is NT$6,084
NT$7,993 total
includes taxes & fees
Aug 21 - Aug 22
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Enjoy a panoramic city view from this stylish room, featuring a spacious dining area with a round table and six comfortable chairs.

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2486)
"Amazing Stay!"
The price is NT$5,672
NT$7,520 total
includes taxes & fees
Aug 3 - Aug 4
Swissotel - Chicago
Loews Chicago Hotel
Hotel entrance with a prominent sign and contemporary design.

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1499)
"Great location and rooms "
The price is NT$5,838
NT$7,784 total
includes taxes & fees
Jul 27 - Jul 28
Loews Chicago Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1940)
"I loved the room pool view, the restaurants & the location "
The price is NT$4,694
NT$5,510 total
includes taxes & fees
Aug 21 - Aug 22
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Relax by the rectangular pool with marked lanes, surrounded by sun loungers and a seating area.

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very Good, (1544)
"Great location and views from rooms were beautiful. "
The price is NT$5,396
NT$7,229 total
includes taxes & fees
Aug 17 - Aug 18
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Enjoy a meal in the kitchen with a large island and dining area, offering a view of the city skyline.

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1825)
"Nice place to stay and explore Chicago."
The price is NT$6,838
NT$8,889 total
includes taxes & fees
Aug 3 - Aug 4
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Conference room with a large, round table and six chairs, offering city views.

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2770)
"Great location and friendly staff"
The price is NT$4,459
NT$5,235 total
includes taxes & fees
Jul 27 - Jul 28
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Stunning city views from a sleek, high-rise building with a dynamic design and lush greenery.

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1013)
"Great location and hotel "
The price is NT$4,642
NT$5,450 total
includes taxes & fees
Aug 5 - Aug 6
Ivy Boutique Hotel
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Experience the hotel's inviting atmosphere, featuring a spacious lobby with large windows, comfortable seating, and a cozy reading nook.

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very Good, (1955)
"Great stay! "
The price is NT$4,013
NT$4,711 total
includes taxes & fees
Aug 17 - Aug 18
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3317)
"Great stay for a short weekend"
The price is NT$6,334
NT$8,296 total
includes taxes & fees
Aug 21 - Aug 22
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Enjoy a sophisticated dining experience with a beautifully set table and city view.

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2525)
"Great location and accommodations! Would definitely stay here again. "
The price is NT$4,214
NT$4,947 total
includes taxes & fees
Aug 10 - Aug 11
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
Experience the grandeur of our lobby, featuring a stunning chandelier, comfortable seating, and a beautiful staircase.

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1906)
"It was a wonderful stay"
The price is NT$3,726
NT$5,063 total
includes taxes & fees
Aug 24 - Aug 25
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Room, 1 King Bed, Corner | Premium bedding, pillowtop beds, in-room safe, desk

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1029)
"Best place we have stayed in Chicago in a long time. "
The price is NT$4,962
NT$6,686 total
includes taxes & fees
Aug 17 - Aug 18
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Experience the vibrant city atmosphere from this unique, circular building with a glass facade offering a glimpse into the interior.

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1122)
"Great stay"
The price is NT$1,191
NT$5,528 total
includes taxes & fees
Aug 4 - Aug 5
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Enjoy meals around the central dining table, surrounded by comfortable chairs and a display case.

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1694)
"I really enjoyed my stay here, the staff was very pleasant and the rooms great!"
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Experience the grand entrance of Riu Plaza Chicago Hotel, marked by a striking canopy and columns.

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2228)
"Great location, great breakfast and perfect rooms."
The price is NT$4,686
NT$6,328 total
includes taxes & fees
Aug 24 - Aug 25
Hotel Riu Plaza Chicago
Best Western Grant Park Hotel
Relax in a stylish seating area with plush armchairs and a decorative partition, surrounded by ambient lighting and a patterned rug.

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2583)
"Excellent Hotel!!"
The price is NT$3,616
NT$4,245 total
includes taxes & fees
Aug 24 - Aug 25
Best Western Grant Park Hotel
Congress Plaza Hotel
Experience grandeur in this beautifully designed ballroom with high ceilings, arched windows, and elegant table settings.

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8957)
"Great place to stay."
The price is NT$5,204
NT$6,109 total
includes taxes & fees
Aug 4 - Aug 5
Congress Plaza Hotel
Le Méridien Essex Chicago
Relax in a spacious room with a large bed, tufted headboard, and comfortable armchair, offering a city view.

Le Méridien Essex Chicago

4.0 star property
8.6 out of 10, Excellent, (1007)
"The staff was so friendly, accommodations were modern and well appointed, a wonderful location with surprisingly good food in the attached restaurant "
The price is NT$4,236
NT$5,413 total
includes taxes & fees
Aug 24 - Aug 25
Le Méridien Essex Chicago
InterContinental Chicago Magnificent Mile by IHG
Experience the hotel's striking entrance with a view of the interior through its large windows and decorative elements.

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
9.0 out of 10, Wonderful, (2099)
"Great hotel"
The price is NT$7,102
NT$9,276 total
includes taxes & fees
Aug 24 - Aug 25
InterContinental Chicago Magnificent Mile by IHG
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.

Top Sleepy Hollow Hotel Reviews

Freehand Chicago

Freehand Chicago

10/10 Excellent
"Good but spooky "
Alexandria 2-night trip
Posted 10 hours ago
Freehand Chicago

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.