Find hotels in Sleepy Hollow, Chicago from ₩144,621

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Discover 4,662 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

Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2292)
"Nice place to stay!"
The price is ₩172,214
₩226,578 total
includes taxes & fees
Sep 23 - Sep 24
Freehand Chicago
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, (2120)
"Great place to stay!"
The price is ₩287,301
₩377,475 total
includes taxes & fees
Sep 22 - Sep 23
Sable at Navy Pier Chicago, Curio Collection by Hilton
Claridge House
Cocktail bar

Claridge House

4.0 star property
9.0 out of 10, Wonderful, (1357)
"We had a great stay"
The price is ₩178,094
₩249,760 total
includes taxes & fees
Sep 21 - Sep 22
Claridge House
Warwick Allerton - Chicago
Ballroom

Warwick Allerton - Chicago

4.0 star property
8.4 out of 10, Very Good, (2916)
"Great location....so close to everything."
The price is ₩149,752
₩216,489 total
includes taxes & fees
Sep 22 - Sep 23
Warwick Allerton - Chicago
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2621)
"Great location."
The price is ₩182,683
₩214,452 total
includes taxes & fees
Sep 22 - Sep 23
Best Western Grant Park Hotel
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2334)
"It was a decent stay nice for someone needing a little roomy room"
The price is ₩184,416
₩216,486 total
includes taxes & fees
Sep 22 - Sep 23
Travelodge by Wyndham Downtown Chicago
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Awesome place to stay. "
The price is ₩167,361
₩196,465 total
includes taxes & fees
Sep 21 - Sep 22
Ohio House Motel
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very Good, (229)
"Great place "
The price is ₩176,645
₩207,363 total
includes taxes & fees
Sep 23 - Sep 24
FOUND Hotel Chicago River North
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1691)
"Very nice hotel. "
The price is ₩162,231
₩200,875 total
includes taxes & fees
Sep 22 - Sep 23
Hotel Saint Clair- Magnificent Mile
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2835)
"Great hotel and location"
The price is ₩222,756
₩261,494 total
includes taxes & fees
Sep 22 - Sep 23
Hilton Chicago/Magnificent Mile Suites
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9139)
"Very nice hotel"
The price is ₩204,973
₩240,617 total
includes taxes & fees
Sep 22 - Sep 23
Congress Plaza Hotel
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1830)
"Amazing place to stay"
The price is ₩193,719
₩227,408 total
includes taxes & fees
Oct 2 - Oct 3
Central Loop Hotel
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, (3580)
"Over all good stay and central location"
The price is ₩189,615
₩222,591 total
includes taxes & fees
Sep 24 - Sep 25
The Whitehall Hotel, BW Premier Collection
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2821)
"It was one of the best hotels I’ve stayed in. "
The price is ₩218,416
₩256,409 total
includes taxes & fees
Sep 14 - Sep 15
Aloft Chicago Mag Mile
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1953)
"Good place to stay"
The price is ₩223,241
₩294,620 total
includes taxes & fees
Sep 14 - Sep 15
Millennium Knickerbocker Chicago
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, (2028)
"Over all good stay . "
The price is ₩231,838
₩272,155 total
includes taxes & fees
Sep 21 - Sep 22
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3049)
"Great location and wonderful views of the city we enjoyed our stay! "
The price is ₩252,581
₩296,503 total
includes taxes & fees
Oct 2 - Oct 3
Eurostars Magnificent Mile
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, (3855)
"Great hotel"
The price is ₩248,311
₩291,490 total
includes taxes & fees
Sep 14 - Sep 15
Hilton Garden Inn Chicago Downtown/Magnificent Mile
The Godfrey Hotel Chicago
American cuisine, alfresco dining

The Godfrey Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1896)
"Loved the stay"
The price is ₩258,114
₩335,558 total
includes taxes & fees
Oct 5 - Oct 6
The Godfrey Hotel Chicago
Club Quarters Hotel, Central Loop, Chicago
Breakfast, lunch and dinner served

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.8 out of 10, Excellent, (3354)
"Quiet and cozy perfect for our stay"
The price is ₩191,413
₩224,699 total
includes taxes & fees
Oct 2 - Oct 3
Club Quarters Hotel, Central 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

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

10/10 Excellent
"Everything just fantastic at the Palmer house! A must place to stay in Chicago!"
Rodney 1-night trip
Posted 4 days ago
Palmer House a Hilton Hotel

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.