Default HTG hotel image

Find hotels in Sleepy Hollow, Chicago

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Sleepy Hollow hotels

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

1. Carleton of Oak Park

Carleton of Oak Park
3.0 star property
6 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (1,166 reviews)
"Rooms were clean and the staff was amazing!"
United States
Suzanne
$135 nightly
The price is $149
Sep 28 - Sep 29
Total with taxes and fees
Carleton of Oak Park
A grand lobby with a central bar, high ceilings, and classical architecture.

2. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 7.2 mi from Sleepy Hollow
8.6 out of 10, Excellent, (1,000 reviews)
"The hotel was absolutely stunning! Loved the convenience of it being right down town!"
United States
Amanda
$135 nightly
The price is $161
Sep 27 - Sep 28
Total with taxes and fees
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
A cozy room with a sofa, a dining table, and a window with a view of buildings.

3. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
6.8 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (286 reviews)
"It was a very nice place to stay"
Canada
chidubem
$166 nightly
The price is $195
Sep 27 - Sep 28
Total with taxes and fees
LIVN - West Loop Chicago
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

4. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 7.3 mi from Sleepy Hollow
8.8 out of 10, Excellent, (3,664 reviews)
"Clean, convenient location for public transit and sights."
United States
Michael
$134 nightly
The price is $159
Sep 27 - Sep 28
Total with taxes and fees
Club Quarters Hotel, Central Loop, Chicago
A multi-story hotel with a prominent sign reading "Crowne Plaza."

5. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
6.7 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (2,665 reviews)
"Great stay, close to great food and ambiance in West Loop."
United States
Victoria
$189 nightly
The price is $224
Sep 27 - Sep 28
Total with taxes and fees
Crowne Plaza Chicago West Loop by IHG
A large, historic building with a central courtyard surrounded by trees.

6. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 7.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,255 reviews)
"Great stay!"
United States
Alan
$208 nightly
The price is $248
Oct 23 - Oct 24
Total with taxes and fees
Hilton Chicago
A modern interior with a bar area, seating, and decorative wooden panels.

7. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 7.1 mi from Sleepy Hollow
8.2 out of 10, Very good, (2,730 reviews)
"Great place to stay. Close to soldier field and has a great little bakery/cafe attached to the downstairs. Clean and great staff!"
United States
Paige
$188 nightly
The price is $224
Sep 27 - Sep 28
Total with taxes and fees
Best Western Grant Park Hotel
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

8. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 7.4 mi from Sleepy Hollow
8.0 out of 10, Very good, (10,192 reviews)
"Easy check in, rooms were clean, convenient location."
United States
John
$188 nightly
The price is $223
Sep 27 - Sep 28
Total with taxes and fees
Congress Plaza Hotel
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

9. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 7.3 mi from Sleepy Hollow
7.8 out of 10, Good, (2,845 reviews)
"Great stay will be returning"
United States
Tremecka
$147 nightly
The price is $175
Sep 27 - Sep 28
Total with taxes and fees
Travelodge by Wyndham Downtown Chicago
A modern hotel with a glass facade, multiple floors, and a prominent sign.

10. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
7.1 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (1,000 reviews)
"Hotel was clean, the room was comfortable and spacious, the amenities were nice, and the breakfast was good. Would stay again."
United States
Rebecca
$206 nightly
The price is $245
Sep 27 - Sep 28
Total with taxes and fees
Hampton Inn Chicago West Loop Fulton Market Area
An outdoor seating area with wicker chairs, a glass-top table, and a sofa with cushions.

11. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 7.4 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (2,775 reviews)
"Great place to stay!"
United States
Tamika
$220 nightly
The price is $262
Sep 27 - Sep 28
Total with taxes and fees
Hyatt Centric The Loop Chicago
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

12. The Wade

The Wade
4.5 star property
Streeterville, 8.6 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,088 reviews)
"Great stay"
United States
Fernanda
$149 nightly
The price is $177
Sep 27 - Sep 28
Total with taxes and fees
The Wade

13. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 7.2 mi from Sleepy Hollow
9.6 out of 10, Exceptional, (1,243 reviews)
"The room was clean and the building was nostalgic."
United States
John
$316 nightly
The price is $376
Oct 14 - Oct 15
Total with taxes and fees
Hilton Vacation Club Hotel Blake Chicago
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

14. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 7.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,296 reviews)
"Great stay overall"
United States
Nathan
$143 nightly
The price is $170
Sep 27 - Sep 28
Total with taxes and fees
Central Loop Hotel
A modern urban building with a distinctive curved facade, a prominent '10pin' sign, and a 'Tertius' restaurant on the ground floor.

15. Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0 star property
River North, 7.8 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (1,002 reviews)
"Great location friendly staff"
United States
Alejandro
$265 nightly
The price is $315
Sep 27 - Sep 28
Total with taxes and fees
Hotel Chicago Downtown, Autograph Collection by Marriott
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

16. River Hotel

River Hotel
4.0 star property
The Loop, 7.9 mi from Sleepy Hollow
8.8 out of 10, Excellent, (5,426 reviews)
"Location is great."
United States
Isabella
$179 nightly
The price is $213
Sep 27 - Sep 28
Total with taxes and fees
River Hotel
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

17. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 7.2 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,004 reviews)
"This hotel was perfect. Room was a great size, clean, very friendly staff. Perfect for our work trip!"
United States
amanda
$214 nightly
The price is $254
Sep 27 - Sep 28
Total with taxes and fees
Le Méridien Essex Chicago
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

18. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
6.6 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,315 reviews)
"A great hotel in a bustling area. We had a great stay."
United States
Joel
$275 nightly
The price is $327
Sep 27 - Sep 28
Total with taxes and fees
Hyatt House Chicago/West Loop-Fulton Market
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

19. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 8.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2,703 reviews)
"Amazing place to stay"
United States
Shanequa
$314 nightly
The price is $374
Sep 27 - Sep 28
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

20. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,009 reviews)
"I was happy with my stay"
United States
Lora J
$179 nightly
The price is $213
Sep 27 - Sep 28
Total with taxes and fees
Fairfield Inn & Suites Chicago Downtown / 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.
View all properties

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow
Learn more about Sleepy Hollow
A cityscape with tall skyscrapers and a historic tower.

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.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

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.

A river with yellow boats, a bridge, and tall buildings.

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.

A large, historic building with a central tower and multiple windows, located near a body of water.

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.

A river with a city skyline in the background, surrounded by green trees and grass.

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 Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"Nice stay"
Christian 1-night trip
Posted less than an hour ago
Hotel Saint Clair- Magnificent Mile

Frequently asked questions

What other neighbourhoods are similar to Sleepy Hollow?
Sleepy Hollow is a suburban village, so other similar areas would be the surrounding towns in the Fox River Valley like West Dundee, East Dundee, and Carpentersville.

West Dundee, located just south of Sleepy Hollow along the Fox River, offers a similar quiet, residential feel with a charming downtown area. This area is great for families looking for a relaxed atmosphere with local parks and community events, and it provides easy access to the river for outdoor activities.

East Dundee, situated across the Fox River from West Dundee, also provides a comparable suburban experience. It features a mix of residential streets and a small, established downtown with local shops and eateries.
What are the best hotels in Sleepy Hollow that travelers recommend?
For a highly recommended hotel in Sleepy Hollow, consider the Carlton Inn Midway.

The Carlton Inn Midway offers a comfortable stay with amenities that guests appreciate. Travelers frequently mention the excellent and free continental breakfast as a highlight, along with the nice and clean rooms. The staff also receives high praise for their friendly and great customer service. The hotel provides air conditioning and premium bedding, ensuring a pleasant and restful experience.
What are the best family hotels in Sleepy Hollow?
For family-friendly hotels in Sleepy Hollow, the Carlton Inn Midway is a highly recommended option.

This hotel offers a range of convenient amenities for families, including complimentary breakfast and free wired internet in public areas. Travelers appreciate the free airport shuttle available 24 hours a day, as well as complimentary self-parking. The hotel also provides free toiletries and free WiFi. Guests consistently praise the excellent and free breakfast, the nice and clean rooms, and the friendly and great staff and customer service.
What hotels in Sleepy Hollow offer free breakfast?
For a hotel in Sleepy Hollow that offers free breakfast, consider the Carlton Inn Midway.

The Carlton Inn Midway provides complimentary breakfast, including continental options, which guests frequently describe as excellent. This hotel also offers a 24-hour free airport shuttle, free self-parking, and free wired internet in public areas, adding to its convenience. Guests consistently praise the clean rooms and the friendly, great staff.
What are the top pet-friendly hotels in Sleepy Hollow?
For a top pet-friendly hotel in Sleepy Hollow, consider the Carlton Inn Midway.

The Carlton Inn Midway welcomes both dogs and cats, making it an ideal choice for travelers with pets. Guests consistently praise the excellent and free breakfast, the nice and clean rooms, and the friendly and great staff. This hotel also offers a complimentary 24-hour airport shuttle, free wired internet in public areas, and free self-parking, adding to its convenience.
What are the best budget hotels in Sleepy Hollow?
For a budget-friendly stay in Sleepy Hollow, the Carlton Inn Midway is an excellent option.

This hotel offers a range of complimentary amenities that enhance its value, including free wired internet in public areas, free breakfast, and free continental breakfast. Guests also benefit from a free airport shuttle service available 24 hours a day and free self-parking. Travelers often praise the excellent and free breakfast, the nice and clean rooms, and the friendly and great staff, highlighting the quality of customer service.
When is the best time to go to Sleepy Hollow?
The best time to go to Sleepy Hollow, Illinois, is during the autumn months, particularly from late September to late October. This period offers pleasant weather and allows visitors to fully experience the area's seasonal offerings.

Autumn in Sleepy Hollow aligns perfectly with events and attractions related to the famous legend. Travelers seeking a festive and atmospheric experience will find the crisp air and fall foliage enhance the local activities, from pumpkin patches to corn mazes. Couples looking for a cozy getaway will appreciate the picturesque surroundings and themed events.

For families, visiting during this time provides ample opportunities for seasonal fun. Many local farms and community centers host family-friendly events with hayrides and apple picking, providing entertainment for all ages.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Sleepy Hollow.
How much is the nightly rate at a Sleepy Hollow hotel?
Prices for hotels in Sleepy Hollow often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Explore a world of travel with Expedia