Find hotels in Sleepy Hollow, Chicago from SAR 697

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Check prices for these dates

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

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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, (2,516 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is SAR 941
SAR 1,248 total
includes taxes & fees
14 Jun - 15 Jun
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very Good, (3,033 reviews)
"Great central location, lots to do nearby."
United States
Michael
The price is SAR 527
SAR 805 total
includes taxes & fees
10 Jun - 11 Jun
Freehand Chicago
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, (1,510 reviews)
"A nice stay and lovely location. "
United States
Robin
The price is SAR 587
SAR 697 total
includes taxes & fees
22 Jun - 23 Jun
The Chicago Hotel Collection Ambassador Gold Coast
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, (10,145 reviews)
"Excellent stay"
United States
Jennifer
The price is SAR 762
SAR 906 total
includes taxes & fees
3 Jun - 4 Jun
Congress Plaza Hotel
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.5 km from Sleepy Hollow
7.8 out of 10, Good, (1,476 reviews)
"Great stay"
United States
Ontario
The price is SAR 714
SAR 849 total
includes taxes & fees
21 Jun - 22 Jun
The Chicago Hotel Collection - Magnificent Mile
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, (2,457 reviews)
"My favorite place to stay!"
United States
Teresa
The price is SAR 1,097
SAR 1,416 total
includes taxes & fees
21 Jun - 22 Jun
Palmer House a Hilton Hotel
Shopping mall

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 13.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,966 reviews)
"Loved everything including location and food options. Great hotel. "
United States
Eileen
The price is SAR 578
SAR 776 total
includes taxes & fees
16 Jun - 17 Jun
Millennium Hotel Knickerbocker Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 11.8 km from Sleepy Hollow
7.4 out of 10, Good, (2,609 reviews)
"Staff was friendly and helpful.. location was great"
United States
Amber
The price is SAR 605
SAR 719 total
includes taxes & fees
3 Jun - 4 Jun
Travelodge by Wyndham Downtown 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, (1,846 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is SAR 1,483
SAR 1,763 total
includes taxes & fees
2 Jun - 3 Jun
The Wade
Exterior detail

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 12.6 km from Sleepy Hollow
8.4 out of 10, Very Good, (625 reviews)
"Excellent stay in good location"
United States
Nicholas
The price is SAR 671
SAR 787 total
includes taxes & fees
15 Jun - 16 Jun
FOUND Hotel Chicago River North
2 restaurants; breakfast, lunch, and dinner served

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, (3,714 reviews)
"Can't beat the location; it's next to Michigan Avenue and across from the Riverwalk; we'd stay there again."
United States
Matson
The price is SAR 862
SAR 1,134 total
includes taxes & fees
21 Jun - 22 Jun
LondonHouse Chicago, Curio Collection by Hilton
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, (2,238 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is SAR 795
SAR 1,059 total
includes taxes & fees
21 Jun - 22 Jun
Silversmith Hotel Chicago Downtown
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,263 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is SAR 897
SAR 1,173 total
includes taxes & fees
16 Jun - 17 Jun
Hotel Riu Plaza 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, (3,580 reviews)
"Great location, large rooms, we loved our stay and would definitely recommend "
Australia
Belinda
The price is SAR 901
SAR 1,071 total
includes taxes & fees
11 Jun - 12 Jun
Eurostars Magnificent Mile
Property entrance

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,042 reviews)
"Great location right off magnificent mile and close to everything. "
United States
Natalia
The price is SAR 769
SAR 1,025 total
includes taxes & fees
17 Jun - 18 Jun
Warwick Allerton - Chicago
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,821 reviews)
"Great staff and location. "
United States
Robert
The price is SAR 966
SAR 1,259 total
includes taxes & fees
16 Jun - 17 Jun
Hilton Chicago
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,277 reviews)
"Happy with our stay!"
United States
Jennifer
The price is SAR 726
SAR 852 total
includes taxes & fees
17 Jun - 18 Jun
Ivy Boutique Hotel
Lobby sitting area

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very Good, (1,945 reviews)
"The staff was super helpful and the rooms were super clean"
United States
Miguel
The price is SAR 647
SAR 782 total
includes taxes & fees
10 Jun - 11 Jun
Hotel Saint Clair- Magnificent Mile
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,244 reviews)
"Really nice stay. "
United States
Rachael Lindsay
The price is SAR 890
SAR 1,058 total
includes taxes & fees
15 Jun - 16 Jun
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Lobby

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,727 reviews)
"Amazing place"
United States
Rodolfo
The price is SAR 554
SAR 774 total
includes taxes & fees
2 Jun - 3 Jun
Hotel Felix River North/Magnificent Mile
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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

8/10 Good
"Staff was professional. Room was clean"
Pierre 1-night trip
Posted 1 hour ago
Hotel Felix River North/Magnificent Mile

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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.