Default HTG hotel image

Sleepy Hollow Hotels, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Filter by

Property class

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
9.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,194 reviews)
"Definitely a boutique hotel, but we'll maintained and in a good area with good eateries close."
United States
Brad
The price is AU$196
includes taxes & fees
27 Oct - 28 Oct
Carleton of Oak Park
A modern interior with a bar area, seating, and decorative wooden panels.

2. 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, (2,757 reviews)
"Clean room, friendly staff, and convenient location."
Canada
Colin
The price is AU$183
includes taxes & fees
10 Nov - 11 Nov
Best Western Grant Park Hotel
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

3. 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, (2,197 reviews)
"Great place to stay at"
United States
Aran
The price is AU$210
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Chicago Downtown South Loop
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

4. 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, (10,162 reviews)
"It was a wonderful stay!"
United States
Ashya
The price is AU$181
includes taxes & fees
10 Nov - 11 Nov
Congress Plaza Hotel
A modern kitchen with a large window, a dining area, and a view of the sea.

5. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,528 reviews)
"Clean room great breakfast loved the pool"
United States
Cynthia
The price is AU$246
includes taxes & fees
10 Nov - 11 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

6. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,221 reviews)
"Great location!"
United States
Mario
The price is AU$294
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

7. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 11.8 km from Sleepy Hollow
7.8 out of 10, Good, (2,927 reviews)
"Great stay"
United States
Sandra
The price is AU$192
includes taxes & fees
11 Nov - 12 Nov
Travelodge by Wyndham Downtown Chicago
A multi-story hotel with a prominent sign reading "Crowne Plaza."

8. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,741 reviews)
"Nice hotel and location was perfect."
United States
Chriselda
The price is AU$275
includes taxes & fees
15 Nov - 16 Nov
Crowne Plaza Chicago West Loop by IHG
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

9. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,451 reviews)
"Friendly staff, great location"
Canada
Anna
The price is AU$332
includes taxes & fees
13 Nov - 14 Nov
Hilton Chicago
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

10. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,443 reviews)
"Convenient location near good restaurants."
United States
Scott
The price is AU$244
includes taxes & fees
9 Nov - 10 Nov
Claridge House Chicago, Tapestry Collection by Hilton
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

11. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
10.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,309 reviews)
"Location was amazing. Loved the outdoor market in walking distance"
United States
Georgianna
The price is AU$334
includes taxes & fees
1 Nov - 2 Nov
Hyatt House Chicago/West Loop-Fulton Market
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

12. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,004 reviews)
"Room was standard, close to millennium park, very helpful staff, & yummy restaurant!"
United States
Caitlin Vania
The price is AU$269
includes taxes & fees
9 Nov - 10 Nov
Le Méridien Essex Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

13. 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, (2,733 reviews)
"Amazing place to stay"
United States
Shanequa
The price is AU$376
includes taxes & fees
12 Nov - 13 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern hotel with a glass facade, multiple floors, and a prominent sign.

14. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,009 reviews)
"Nice location, good breakfast Comfortable beds"
United States
Terri
The price is AU$364
includes taxes & fees
30 Oct - 31 Oct
Hampton Inn Chicago West Loop Fulton Market Area
A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.

15. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice place"
United States
Brock
The price is AU$330
includes taxes & fees
30 Oct - 31 Oct
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
A building with a stone facade and large glass windows.

16. Ohio House Motel

Ohio House Motel
3.0 star property
River North, 12.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,225 reviews)
"Really cute little motel close to the loop! Was great to stay here with friends and the staff were wonderful."
United States
Sarah
The price is AU$185
includes taxes & fees
15 Nov - 16 Nov
Ohio House Motel
A rooftop terrace with lounge chairs and tables, offering a city skyline view.

17. Best Western River North Hotel

Best Western River North Hotel
2.5 star property
River North, 12.6 km from Sleepy Hollow
7.8 out of 10, Good, (1,192 reviews)
"it was a little more outdated than we thought from the pictures we saw but it was still very clean and staff was very helpful"
United States
Jordan
The price is AU$202
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
A spacious lobby with a central coffee table, sofas, and a large mirror.

18. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
13.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,536 reviews)
"Nice Hotel and location!"
United States
Christian
The price is AU$206
includes taxes & fees
11 Nov - 12 Nov
The Chicago Hotel Collection Ambassador Gold Coast
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

19. 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, (2,716 reviews)
"Beautiful hotel with wonderful staff!"
United States
Christy
The price is AU$368
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

20. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (3,667 reviews)
"perfect stay, would recommend"
United States
David
The price is AU$253
includes taxes & fees
25 Oct - 26 Oct
Club Quarters Hotel, Central Loop, Chicago
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

Our guide on where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Sleepy Hollow Hotel Reviews

Recent Reviews in Sleepy Hollow

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Staff was friendly and helpful! Gave my family and I great ideas for restaurants!"
Patrice 4-night trip
Posted 1 hour ago
L7 Chicago by LOTTE

Frequently asked questions

What are the best hotels in Sleepy Hollow that travellers recommend?
For hotels in Sleepy Hollow that travellers frequently recommend, consider the Carlton Inn Midway.

The Carlton Inn Midway is praised by guests for its excellent complimentary breakfast and its nice, clean rooms. The staff are often described as friendly and providing great customer service. This hotel offers premium bedding and air conditioning, ensuring a comfortable stay. Its location within a shopping district adds convenience for guests.
What are the best family hotels in Sleepy Hollow?
For a family-friendly hotel in Sleepy Hollow, the Carlton Inn Midway is a highly recommended option.

The Carlton Inn Midway offers a range of convenient amenities for families, including complimentary continental breakfast and free WiFi. Guests appreciate the free wired internet in public areas, and free self-parking is also available. For those travelling with infants, a free crib can be provided. The hotel also offers a complimentary 24-hour airport shuttle, making arrivals and departures straightforward. Guests frequently mention the excellent and free breakfast, along with the nice, clean rooms and friendly, great staff.
What hotels in Sleepy Hollow offer free breakfast?
For hotels in Sleepy Hollow that offer free breakfast, the Carlton Inn Midway is a highly recommended option.

The Carlton Inn Midway provides a complimentary breakfast, with guests frequently praising the excellent quality of the breakfast offerings. This hotel also offers free WiFi, free self-parking, and a 24-hour airport shuttle service, making it a convenient choice for travellers. Their rooms are often described as nice and clean, and the staff consistently receives commendations for being friendly and providing great customer service.
What are the top pet-friendly hotels in Sleepy Hollow?
For a top pet-friendly hotel in Sleepy Hollow, the Carlton Inn Midway is a great option.

The Carlton Inn Midway welcomes both dogs and cats. This hotel offers complimentary wired internet in public areas and free WiFi, along with a free continental breakfast and free self-parking. For added convenience, there is a 24-hour free airport shuttle and complimentary toiletries. Guests consistently praise the excellent and free breakfast, the nice and clean rooms, and the friendly and great staff.
What are the best budget hotels in Sleepy Hollow?
For budget-friendly accommodation in Sleepy Hollow, the Carlton Inn Midway is an excellent choice.

This hotel offers a range of convenient amenities, including free WiFi, complimentary continental breakfast, and free self-parking. Guests frequently mention the excellent and free breakfast, nice and clean rooms, and the friendly and great staff. For added convenience, the hotel provides a 24-hour free airport shuttle service and free toiletries.
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, with mild temperatures and colourful foliage, making it ideal for outdoor activities and exploring the area. The days are generally sunny, providing comfortable conditions for walks and visits to local attractions.

For families, visiting in October is particularly good due to the many Halloween-themed events and activities that take place. These often include pumpkin patches, corn mazes, and special community gatherings that are very popular with children and offer a memorable holiday experience.

Couples looking for a relaxing escape will also appreciate the autumn.
Can I cancel my hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline − this is often within 24 to 48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our 'Fully refundable property' filter during your search to find the right Sleepy Hollow hotel for you.
How can I save on a hotel booking in Sleepy Hollow with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Sleepy Hollow hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Sleepy Hollow?
Hotel prices in Sleepy Hollow often vary, but you can find a great deal on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates and sort search results by 'Price: low to high' for our cheapest rates.

Explore a world of travel with Expedia