Default HTG hotel image

Find hotels in Sleepy Hollow, Chicago

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Sleepy Hollow hotels

1. 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, (2,543 reviews)
"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
United States
Deborah
The price is NT$6,747
NT$9,112 total
includes taxes & fees
Jun 30 - Jul 1
Sable at Navy Pier Chicago, Curio Collection by Hilton

2. Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 13.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,806 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is NT$4,023
NT$5,835 total
includes taxes & fees
Jul 1 - Jul 2
Omni Chicago Hotel

3. 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, (10,253 reviews)
"Great stay thanks"
United States
Felipa
The price is NT$4,300
NT$5,112 total
includes taxes & fees
Jun 29 - Jun 30
Congress Plaza Hotel

4. 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, (2,497 reviews)
"Beautiful place to stay."
United States
Charles Otto
The price is NT$7,086
NT$9,364 total
includes taxes & fees
Jul 1 - Jul 2
Palmer House a Hilton Hotel

5. 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, (4,430 reviews)
"The breakfast, location, and staff were amazing."
United States
Corey
The price is NT$5,059
NT$6,916 total
includes taxes & fees
Jul 6 - Jul 7
Hotel Riu Plaza Chicago

6. 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, (2,638 reviews)
"Great location and helpful staff."
United States
Ming
The price is NT$4,275
NT$5,083 total
includes taxes & fees
Jul 1 - Jul 2
Travelodge by Wyndham Downtown Chicago

7. 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, (1,092 reviews)
"Such a lovely hotel with a beautiful, excellent staff, and lots of character!"
United States
Debby
The price is NT$4,396
NT$6,164 total
includes taxes & fees
Jul 6 - Jul 7
Staypineapple, An Iconic Hotel, The Loop

8. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,382 reviews)
"The property was clean and the location was perfect!"
United States
Martha
The price is NT$5,567
NT$7,733 total
includes taxes & fees
Jul 1 - Jul 2
Swissotel - Chicago

9. 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, (2,246 reviews)
"Great location"
United States
Gabino
The price is NT$4,449
NT$6,255 total
includes taxes & fees
Jul 5 - Jul 6
Silversmith Hotel Chicago Downtown

10. The Blackstone, Autograph Collection

The Blackstone, Autograph Collection
4.0 star property
The Loop, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,009 reviews)
"Great location, clean hotel, and very accommodating staff."
United States
Neydee
The price is NT$4,910
NT$6,766 total
includes taxes & fees
Jul 6 - Jul 7
The Blackstone, Autograph Collection

11. 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, (3,735 reviews)
"Great location, excellent room and amenities proactively attentive staff."
United States
Robert
The price is NT$6,690
NT$8,883 total
includes taxes & fees
Jul 1 - Jul 2
LondonHouse Chicago, Curio Collection by Hilton

12. Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,642 reviews)
"Had an amazing stay here!"
United States
Audrey
The price is NT$4,555
NT$5,415 total
includes taxes & fees
Jul 2 - Jul 3
Eurostars Magnificent Mile

13. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very Good, (2,727 reviews)
"Clean, working air conditioner, and great staff. Very good location as well."
United States
Alexandra
The price is NT$3,771
NT$4,483 total
includes taxes & fees
Jul 1 - Jul 2
Best Western Grant Park Hotel

14. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,414 reviews)
"Great stay!"
United States
Avradita
The price is NT$5,058
NT$6,014 total
includes taxes & fees
Jun 30 - Jul 1
Hilton Chicago/Magnificent Mile Suites

15. 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, (1,596 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is NT$4,944
NT$5,878 total
includes taxes & fees
Jul 1 - Jul 2
The Chicago Hotel Collection Ambassador Gold Coast

16. 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, (1,663 reviews)
"Location was great"
United States
Pamela
The price is NT$6,300
NT$8,618 total
includes taxes & fees
Jul 5 - Jul 6
Sheraton Grand Chicago Riverwalk

17. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,509 reviews)
"Staff was great."
United States
Marianne
The price is NT$7,592
NT$10,154 total
includes taxes & fees
Jul 2 - Jul 3
Hyatt Regency Chicago

18. 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, (2,040 reviews)
"Great hotel, clean efficient and not too far from Downtown would stay again!"
United States
Justin
The price is NT$5,321
NT$6,326 total
includes taxes & fees
Jul 6 - Jul 7
Hilton Garden Inn Chicago Downtown South Loop

19. Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
River North, 13.1 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,597 reviews)
"Great stay"
United States
Matt
The price is NT$4,459
NT$6,241 total
includes taxes & fees
Jul 1 - Jul 2
Hotel 55 Chicago Downtown

20. 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, (2,193 reviews)
"Rooms were clean and staff was very nice"
United States
Mohammed Izzal
The price is NT$6,405
NT$8,744 total
includes taxes & fees
Jul 6 - Jul 7
Fairmont Chicago at Millennium Park
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

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

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.

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

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

Explore a world of travel with Expedia