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Sep 4 - Sep 5
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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.

Our top choices for Sleepy Hollow hotels

River Hotel
Reception

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4603)
"Great place to stay, staff was very friendly"
The price is ￥23,392
￥27,459 total
includes taxes & fees
Sep 14 - Sep 15
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, (2011)
"Overall a nice place to stay."
The price is ￥24,754
￥29,059 total
includes taxes & fees
Sep 22 - Sep 23
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3041)
"Great stay!"
The price is ￥26,862
￥31,533 total
includes taxes & fees
Oct 5 - Oct 6
Eurostars 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, (2130)
"Great place to stay!"
The price is ￥29,492
￥38,912 total
includes taxes & fees
Sep 14 - Sep 15
Sable at Navy Pier Chicago, Curio Collection by Hilton
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3713)
"Great place to stay "
The price is ￥26,929
￥31,612 total
includes taxes & fees
Sep 22 - Sep 23
citizenM Chicago Downtown
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2157)
"Amazing stay and great location…"
The price is ￥27,229
￥36,308 total
includes taxes & fees
Sep 11 - Sep 12
Hilton 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, (3812)
"Great place to stay "
The price is ￥24,089
￥28,278 total
includes taxes & fees
Sep 14 - Sep 15
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9159)
"Great place to stay! Wonderful staff and ambience and walkable to many things. "
The price is ￥21,886
￥25,692 total
includes taxes & fees
Sep 22 - Sep 23
Congress Plaza Hotel
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2804)
"Close to everything, easy check-in/out and friendly staff!"
The price is ￥21,972
￥25,793 total
includes taxes & fees
Sep 21 - Sep 22
Aloft Chicago Mag Mile
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1025)
"The hotel is a bit outdated but decent. The location is very good, easy access to many good areas around it."
The price is ￥21,267
￥24,965 total
includes taxes & fees
Oct 2 - Oct 3
Best Western River North Hotel
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2283)
"Nice place to stay!"
The price is ￥15,814
￥21,172 total
includes taxes & fees
Sep 23 - Sep 24
Freehand Chicago
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2786)
"Great staff clean rooms and good location"
The price is ￥23,801
￥27,940 total
includes taxes & fees
Sep 24 - Sep 25
Hilton Chicago/Magnificent Mile Suites
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, (1007)
"Staff was very friendly The rooftop pool was really nice. "
The price is ￥25,020
￥31,150 total
includes taxes & fees
Oct 5 - Oct 6
Holiday Inn & Suites Chicago - Downtown by IHG
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
9.0 out of 10, Wonderful, (1450)
"Great place to stay. "
The price is ￥28,801
￥33,809 total
includes taxes & fees
Sep 28 - Sep 29
Crowne Plaza Chicago West Loop by IHG
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.0 out of 10, Very Good, (223)
"Great place "
The price is ￥17,595
￥20,653 total
includes taxes & fees
Sep 24 - Sep 25
FOUND Hotel Chicago River North
Regal Inn - Chicago O'Hare Airport
Lobby

Regal Inn - Chicago O'Hare Airport

2.0 star property
8.0 out of 10, Very Good, (1001)
"Was a nice place with a great restaurant right around the corner. Would stay again. "
The price is ￥10,689
￥11,435 total
includes taxes & fees
Sep 10 - Sep 11
Regal Inn - Chicago O'Hare Airport
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2388)
"Enjoyed our stay "
The price is ￥27,753
￥36,752 total
includes taxes & fees
Oct 1 - Oct 2
Hotel Riu Plaza Chicago
The Whitehall Hotel, BW Premier Collection
Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very Good, (3543)
"Clean room, great A/C. Breakfast was good as well."
The price is ￥18,972
￥22,272 total
includes taxes & fees
Sep 24 - Sep 25
The Whitehall Hotel, BW Premier Collection
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, (2525)
"Had a wonderful stay here and staff was super friendly!"
The price is ￥27,848
￥35,298 total
includes taxes & fees
Sep 14 - Sep 15
La Quinta Inn & Suites by Wyndham Chicago Downtown
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2099)
"Property was great, very clean and friendly staff. The location is wonderful. Will definitely stay here again. "
The price is ￥31,826
￥37,360 total
includes taxes & fees
Sep 12 - Sep 13
Hyatt Centric The Loop Chicago
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

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

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"loved our stay, great hotel and friendly staff"
Jared 2-night trip
Posted 18 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.