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Aug 17 - Aug 18
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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.

Holiday Inn Express Chicago - Magnificent Mile by IHG
Exterior

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very Good, (1006)
"Great stay"
The price is NT$4,319
NT$5,071 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Chicago - Magnificent Mile by IHG
The Chicago Hotel Collection Ambassador Gold Coast
Terrace/patio

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very Good, (1085)
"Beautiful hotel, we were able to walk everywhere we needed to get to! tons of shopping and food close by. "
The price is NT$4,588
NT$5,386 total
includes taxes & fees
Aug 18 - Aug 19
The Chicago Hotel Collection Ambassador Gold Coast
L7 Chicago by LOTTE
Exterior

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (2820)
"Excellent hotel in a great location."
The price is NT$7,022
NT$8,243 total
includes taxes & fees
Sep 1 - Sep 2
L7 Chicago by LOTTE
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1306)
"He a great time, clean hotel"
The price is NT$4,832
NT$6,553 total
includes taxes & fees
Aug 18 - Aug 19
Claridge House
River Hotel
Lobby

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4526)
"Great stay and great location"
The price is NT$4,409
NT$5,176 total
includes taxes & fees
Aug 24 - Aug 25
River Hotel
ACME Hotel Company
Cocktail bar

ACME Hotel Company

3.5 star property
9.0 out of 10, Wonderful, (1755)
"Great place"
The price is NT$4,292
NT$5,039 total
includes taxes & fees
Aug 24 - Aug 25
ACME Hotel Company
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1937)
"Great stay"
The price is NT$3,809
NT$5,176 total
includes taxes & fees
Aug 24 - Aug 25
Millennium Knickerbocker Chicago
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Everyone was nice and a great location "
The price is NT$3,564
NT$4,183 total
includes taxes & fees
Aug 24 - Aug 25
Ohio House Motel
Pendry Chicago
View from property

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1055)
"Wonderful Stay."
The price is NT$7,049
NT$9,507 total
includes taxes & fees
Aug 31 - Sep 1
Pendry Chicago
The Chicago Hotel Collection - Magnificent Mile
Rooftop terrace

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.4 out of 10, Good, (1167)
"Very enjoyable stay"
The Chicago Hotel Collection - 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, (2075)
"Great place to stay!"
The price is NT$4,895
NT$6,616 total
includes taxes & fees
Sep 1 - Sep 2
Sable at Navy Pier Chicago, Curio Collection by Hilton
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, (2474)
"Had a wonderful stay here and staff was super friendly!"
The price is NT$4,022
NT$5,250 total
includes taxes & fees
Sep 1 - Sep 2
La Quinta Inn & Suites by Wyndham Chicago Downtown
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (268)
"Great place. Good stay for family vacation to Chicago"
Level Chicago Fulton Market
The Godfrey Hotel Chicago
American cuisine, alfresco dining

The Godfrey Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1893)
"Loved the stay"
The price is NT$4,469
NT$5,951 total
includes taxes & fees
Sep 2 - Sep 3
The Godfrey Hotel Chicago
The Emily Hotel
Exterior

The Emily Hotel

4.0 star property
9.2 out of 10, Wonderful, (1182)
"Friendly staff, rooms very clean, food was excellent "
The price is NT$15,622
NT$18,339 total
includes taxes & fees
Aug 29 - Aug 30
The Emily Hotel
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2310)
"Beautiful hotel , breakfast was amazing "
The price is NT$4,769
NT$6,444 total
includes taxes & fees
Sep 2 - Sep 3
Hotel Riu Plaza 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, (3706)
"Our stay was wonderful."
The price is NT$4,562
NT$5,356 total
includes taxes & fees
Aug 25 - Aug 26
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Club Quarters Hotel Wacker at Michigan, Chicago
Lobby sitting area

Club Quarters Hotel Wacker at Michigan, Chicago

4.0 star property
8.6 out of 10, Excellent, (1791)
"Fabulous location, Happy helpful staff, great place to stay!"
The price is NT$4,409
NT$5,176 total
includes taxes & fees
Aug 24 - Aug 25
Club Quarters Hotel Wacker at Michigan, Chicago
Embassy Suites by Hilton Chicago Downtown River North
Lobby

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.4 out of 10, Very Good, (4718)
"a great stay"
The price is NT$4,819
NT$5,657 total
includes taxes & fees
Sep 3 - Sep 4
Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Reception

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2605)
"Hotel is amazing "
The price is NT$5,176
NT$6,957 total
includes taxes & fees
Aug 21 - Aug 22
Swissotel - 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 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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Very happy with the hotel and location. We had a double room with two bathrooms. I’ll never understand hotels using full size beds when there’s plenty of room for a queen. The room was large enough to accommodate bigger beds. Luckily it was just me and my 6 year old for this trip so it was great. The hotel offered some nice amenities that we unfortunately didn’t have time to use. The second bathroom was a nice perk of the room. The beds were comfortable enough. Not too hard and not too springy. The hotel is lovely. Beautiful old architecture and the lobby is stunning! "
Anonymous traveler 1-night trip
Posted 10 hours ago
Hilton 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.