Find hotels in Sleepy Hollow, Chicago from AED 154

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Check prices for these dates

Tonight
16 Jun - 17 Jun
Tomorrow
17 Jun - 18 Jun
This weekend
20 Jun - 22 Jun
Next weekend
27 Jun - 29 Jun

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Discover 4,656 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, (2053)
"Amazing stay"
The price is AED 638
AED 855 total
includes taxes & fees
1 Jul - 2 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
Swissotel - Chicago
Front of property - evening/night

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2242)
"Wonderful stay!"
The price is AED 548
AED 751 total
includes taxes & fees
30 Jun - 1 Jul
Swissotel - Chicago
Loews Chicago Hotel
Exterior

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1457)
"Great location and rooms "
The price is AED 621
AED 845 total
includes taxes & fees
30 Jun - 1 Jul
Loews Chicago 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, (1872)
"Great location, friendly staff "
The price is AED 590
AED 693 total
includes taxes & fees
30 Jun - 1 Jul
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free cabanas, sun loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1444)
"Stayed here a few times and its always great. "
The price is AED 675
AED 905 total
includes taxes & fees
29 Jun - 30 Jun
Radisson Blu Aqua Hotel Chicago
Fairmont Chicago at Millennium Park
Exterior

Fairmont Chicago at Millennium Park

4.5 star property
8.6 out of 10, Excellent, (1778)
"Great location ! And hotel felt very welcoming and comfortable. "
The price is AED 757
AED 996 total
includes taxes & fees
6 Jul - 7 Jul
Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile
Exterior

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2759)
"Great hotel and location! "
The price is AED 459
AED 539 total
includes taxes & fees
2 Jul - 3 Jul
Aloft Chicago Mag Mile
Ivy Boutique Hotel
Front of property

Ivy Boutique Hotel

4.5 star property
8.8 out of 10, Excellent, (1003)
"The Ivy Hotel was so nice! It was very roomy and had everything to make our stay convenient and special! "
The price is AED 528
AED 619 total
includes taxes & fees
30 Jun - 1 Jul
Ivy Boutique Hotel
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, (1816)
"Had a wonderful stay"
The price is AED 502
AED 590 total
includes taxes & fees
7 Jul - 8 Jul
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, (3252)
"Room, service and restaurant were top notch."
The price is AED 687
AED 914 total
includes taxes & fees
6 Jul - 7 Jul
Hyatt Regency Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2307)
"Great stay "
The price is AED 509
AED 597 total
includes taxes & fees
8 Jul - 9 Jul
Hilton Chicago/Magnificent Mile Suites
Millennium Knickerbocker Chicago
View from property

Millennium Knickerbocker Chicago

4.0 star property
8.4 out of 10, Very Good, (1839)
"Nice hotel! "
The price is AED 437
AED 599 total
includes taxes & fees
6 Jul - 7 Jul
Millennium Knickerbocker Chicago
Hyatt Centric Chicago Magnificent Mile
Exterior

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1016)
"A great place to stay"
The price is AED 621
AED 836 total
includes taxes & fees
29 Jun - 30 Jun
Hyatt Centric Chicago Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Restaurant

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1093)
"Great stay! "
The price is AED 154
AED 694 total
includes taxes & fees
29 Jun - 30 Jun
The Chicago Hotel Collection - Magnificent Mile
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1624)
"A great stay for the price"
Hotel Saint Clair- Magnificent Mile
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2032)
"Absolutely stunning place to stay. "
The price is AED 532
AED 729 total
includes taxes & fees
29 Jun - 30 Jun
Hotel Riu Plaza Chicago
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2526)
"Great stay"
The price is AED 421
AED 495 total
includes taxes & fees
1 Jul - 2 Jul
Best Western Grant Park Hotel
Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (8897)
"Great place to stay."
The price is AED 526
AED 617 total
includes taxes & fees
3 Jul - 4 Jul
Congress Plaza Hotel
Le Méridien Essex Chicago
City view

Le Méridien Essex Chicago

4.0 star property
8.6 out of 10, Excellent, (1006)
"Great place for price and location "
The price is AED 485
AED 624 total
includes taxes & fees
29 Jun - 30 Jun
Le Méridien Essex Chicago
InterContinental Chicago Magnificent Mile by IHG
Exterior

InterContinental Chicago Magnificent Mile by IHG

4.5 star property
9.0 out of 10, Wonderful, (1880)
"Great hotel location and service excellent ! "
The price is AED 654
AED 885 total
includes taxes & fees
30 Jun - 1 Jul
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.
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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.

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.