Find hotels in Sleepy Hollow, Chicago from SAR 322

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31 Aug - 1 Sep
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1 Sep - 2 Sep
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5 Sep - 7 Sep
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12 Sep - 14 Sep

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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.

FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very Good, (216)
"Great place "
The price is SAR 409
SAR 480 total
includes taxes & fees
2 Sep - 3 Sep
FOUND Hotel Chicago River North
Ohio House Motel
Reception

Ohio House Motel

3.0 star property
9.0 out of 10, Wonderful, (1011)
"Awesome place to stay. "
The price is SAR 413
SAR 485 total
includes taxes & fees
2 Sep - 3 Sep
Ohio House Motel
Level Chicago Fulton Market
Executive lounge

Level Chicago Fulton Market

4.0 star property
9.2 out of 10, Wonderful, (276)
"The staff was excellent the amenities were a fantastic overall a great experience "
The price is SAR 847
SAR 1,078 total
includes taxes & fees
2 Sep - 3 Sep
Level Chicago Fulton Market
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, (1026)
"Great hotel! "
The price is SAR 615
SAR 722 total
includes taxes & fees
2 Sep - 3 Sep
Holiday Inn Express Chicago - Magnificent Mile by IHG
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2331)
"I had a very good stay 10 out of 10 recommend"
The price is SAR 368
SAR 432 total
includes taxes & fees
2 Sep - 3 Sep
Travelodge by Wyndham Downtown Chicago
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very Good, (2625)
"Great hotel! "
The price is SAR 431
SAR 505 total
includes taxes & fees
4 Sep - 5 Sep
Best Western Grant Park Hotel
Pendry Chicago
View from property

Pendry Chicago

4.5 star property
9.4 out of 10, Exceptional, (1068)
"Wonderful Stay."
The price is SAR 882
SAR 1,189 total
includes taxes & fees
21 Sep - 22 Sep
Pendry Chicago
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very Good, (9095)
"Family had a great stay. "
The price is SAR 740
SAR 868 total
includes taxes & fees
15 Sep - 16 Sep
Congress Plaza Hotel
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3679)
"Great place to stay "
The price is SAR 539
SAR 633 total
includes taxes & fees
2 Sep - 3 Sep
citizenM Chicago Downtown
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very Good, (2265)
"Great stay "
The price is SAR 322
SAR 444 total
includes taxes & fees
3 Sep - 4 Sep
Freehand Chicago
The Chicago Hotel Collection River North
Building design

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (579)
"It was a wonderful place to stay! "
The price is SAR 478
SAR 561 total
includes taxes & fees
2 Sep - 3 Sep
The Chicago Hotel Collection River North
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

4.0 star property
9.6 out of 10, Exceptional, (1032)
"Great stay"
The price is SAR 657
SAR 772 total
includes taxes & fees
22 Sep - 23 Sep
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Hilton Chicago
Exterior

Hilton Chicago

4.0 star property
8.4 out of 10, Very Good, (2150)
"Amazing stay and great location…"
The price is SAR 690
SAR 920 total
includes taxes & fees
11 Sep - 12 Sep
Hilton Chicago
Residence Inn Chicago Downtown Magnificent Mile
Aerial view

Residence Inn Chicago Downtown Magnificent Mile

4.0 star property
9.6 out of 10, Exceptional, (334)
"Enjoyable stay at this Hotel in a very large room close to all the sights and shopping."
The price is SAR 859
SAR 1,009 total
includes taxes & fees
2 Sep - 3 Sep
Residence Inn Chicago Downtown Magnificent Mile
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1836)
"Amazing place to stay"
The price is SAR 484
SAR 568 total
includes taxes & fees
2 Sep - 3 Sep
Central Loop Hotel
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very Good, (1913)
"Helpful staff, beautiful hotel in a great location!"
The price is SAR 788
SAR 1,019 total
includes taxes & fees
25 Sep - 26 Sep
Palmer House a Hilton Hotel
Kimpton Gray Hotel by IHG
Dinner served, Argentinean cuisine

Kimpton Gray Hotel by IHG

4.5 star property
9.2 out of 10, Wonderful, (1011)
"Great stay!"
The price is SAR 794
SAR 1,042 total
includes taxes & fees
5 Sep - 6 Sep
Kimpton Gray Hotel by IHG
Club Quarters Hotel, Central Loop, Chicago
Breakfast, lunch and dinner served

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3373)
"Great location, quiet rooms "
The price is SAR 484
SAR 568 total
includes taxes & fees
2 Sep - 3 Sep
Club Quarters Hotel, Central Loop, Chicago
Hotel Saint Clair- Magnificent Mile
Restaurant

Hotel Saint Clair- Magnificent Mile

4.0 star property
8.2 out of 10, Very Good, (1706)
"Had a great stay! The area is very walkable and convenient!!"
Hotel Saint Clair- Magnificent Mile
Chicago Athletic Association, a Hyatt Hotel
Exterior

Chicago Athletic Association, a Hyatt Hotel

4.5 star property
9.0 out of 10, Wonderful, (1002)
"Fantastic place to stay….close to the lake, shopping and dining."
The price is SAR 835
SAR 1,111 total
includes taxes & fees
2 Sep - 3 Sep
Chicago Athletic Association, a Hyatt Hotel
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

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

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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.