Find hotels in Sleepy Hollow, Chicago from SAR 563

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Check prices for these dates

Tonight
8 May - 9 May
Tomorrow
9 May - 10 May
This weekend
8 May - 10 May
Next weekend
15 May - 17 May

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Our top choices for Sleepy Hollow hotels

Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,493 reviews)
"Great place to stay "
United States
Mark
The price is SAR 692
SAR 952 total
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,780 reviews)
"Clean room and great location "
United States
Diana
The price is SAR 596
SAR 819 total
includes taxes & fees
26 May - 27 May
Hilton Chicago
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,151 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is SAR 722
SAR 992 total
includes taxes & fees
26 May - 27 May
Fairmont Chicago at Millennium Park
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,258 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is SAR 447
SAR 646 total
includes taxes & fees
25 May - 26 May
Silversmith Hotel Chicago Downtown
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (10,186 reviews)
"Great stay"
United States
Matthew
The price is SAR 501
SAR 596 total
includes taxes & fees
9 May - 10 May
Congress Plaza Hotel
Exterior

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,513 reviews)
"Clean room , nice staff, nice view"
United States
John Hok-Lam
The price is SAR 765
SAR 1,044 total
includes taxes & fees
25 May - 26 May
Hyatt Regency Chicago
Room service - dining

The Wade

The Wade
4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very Good, (1,831 reviews)
"We enjoy our stay."
United States
Nuria
The price is SAR 634
SAR 754 total
includes taxes & fees
25 May - 26 May
The Wade
Pool

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,985 reviews)
"Had a great stay-5 stars of 5"
United States
donald
The price is SAR 474
SAR 563 total
includes taxes & fees
26 May - 27 May
Hilton Garden Inn Chicago Downtown South Loop
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,627 reviews)
"It was very clean, beautiful place"
United States
Grisel
The price is SAR 807
SAR 1,093 total
includes taxes & fees
25 May - 26 May
Sheraton Grand Chicago Riverwalk
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,310 reviews)
"Breakfasr good, view great"
United States
Jan
The price is SAR 687
SAR 949 total
includes taxes & fees
9 May - 10 May
Swissotel - Chicago
2 restaurants, breakfast, lunch, dinner served; American cuisine

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,707 reviews)
"Amazing hotel and staff!"
United States
erin
The price is SAR 704
SAR 948 total
includes taxes & fees
25 May - 26 May
LondonHouse Chicago, Curio Collection by Hilton
Indoor pool

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 12.1 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,431 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is SAR 555
SAR 771 total
includes taxes & fees
25 May - 26 May
Palmer House a Hilton Hotel
In-room safe, iron/ironing board, free WiFi, bed sheets

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Theatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,396 reviews)
"Very friendly staff, great location."
Canada
Annabel
The price is SAR 625
SAR 849 total
includes taxes & fees
25 May - 26 May
Sports Illustrated Resorts Chicago
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,514 reviews)
"The hotel was phenomenally clean, the staff was nice !"
United States
Rochelle
The price is SAR 540
SAR 642 total
includes taxes & fees
10 May - 11 May
Eurostars Magnificent Mile
Indoor pool

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 13 km from Sleepy Hollow
9.2 out of 10, Wonderful, (3,047 reviews)
"Great stay all around "
United States
Logan
The price is SAR 746
SAR 1,019 total
includes taxes & fees
26 May - 27 May
InterContinental Chicago Magnificent Mile by IHG
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,061 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is SAR 499
SAR 704 total
includes taxes & fees
26 May - 27 May
Staypineapple, An Iconic Hotel, The Loop
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,114 reviews)
"Great breakfast and staff. "
United States
Kelly
The price is SAR 503
SAR 711 total
includes taxes & fees
26 May - 27 May
Arlo Chicago
Terrace/patio

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,457 reviews)
"Clean and friendly staff. "
United States
Bianca
The price is SAR 551
SAR 655 total
includes taxes & fees
26 May - 27 May
DoubleTree by Hilton Chicago - Magnificent Mile
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 13.9 km from Sleepy Hollow
8.2 out of 10, Very Good, (1,423 reviews)
"Great stay, love the surrounding area. Rooms a bit small but overall a great stay. "
United States
Eric
The price is SAR 540
SAR 642 total
includes taxes & fees
10 May - 11 May
The Chicago Hotel Collection Ambassador Gold Coast
Lobby

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,183 reviews)
"Perfect for couples and the location is amazing"
United States
Jaden
The price is SAR 539
SAR 641 total
includes taxes & fees
25 May - 26 May
River 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.
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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

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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

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

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.

Panoramic view of Lincoln Park and the Chicago skyline.

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

Congress Plaza Hotel

Congress Plaza Hotel

8/10 Good
"The hotel looks really cool as it’s really old. The rooms are very basic, a coffee maker and a tiny tv. The south tower is right on the train line so it can be noisy with the train rattling past. The staff was nice. We didn’t use many of the amenities (like restaurants) so I can’t comment on them. The location is great for touring around Chicago as you’re right downtown on Michigan Ave"
Kelly 2-night trip
Posted 1 hour ago
Congress Plaza Hotel

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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?
Hawthorne Works Museum, Jedlica Performing Arts Center, and Balzekas Museum of Lithuanian Culture are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Wintrust Sports Complex and Firehouse Community Arts Center of Chicago are also worth a stop.