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This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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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, (1,188 reviews)
"Definitely a boutique hotel, but we'll maintained and in a good area with good eateries close."
United States
Brad
The price is £103
includes taxes & fees
14 Oct - 15 Oct
Carleton of Oak Park
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

2. 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, (10,189 reviews)
"It was a wonderful stay!"
United States
Ashya
The price is £95
includes taxes & fees
12 Nov - 13 Nov
Congress Plaza Hotel
A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

3. 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, (1,003 reviews)
"Amazing location, super helpful staff, and clean/comfortable rooms. I stay here every time I am in town."
United States
Kayla Rene
The price is £121
includes taxes & fees
11 Nov - 12 Nov
Le Méridien Essex Chicago
A modern interior with a bar area, seating, and decorative wooden panels.

4. 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, (2,754 reviews)
"Excellent stay at a reasonably priced hotel. Will stay again!"
United States
Shelby Ryann
The price is £113
includes taxes & fees
9 Nov - 10 Nov
Best Western Grant Park Hotel
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

5. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
8.6 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,451 reviews)
"Convenient location near good restaurants."
United States
Scott
The price is £129
includes taxes & fees
9 Nov - 10 Nov
Claridge House Chicago, Tapestry Collection by Hilton
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.

6. 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, (2,912 reviews)
"Great stay"
United States
Sandra
The price is £102
includes taxes & fees
12 Nov - 13 Nov
Travelodge by Wyndham Downtown Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

7. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 7.1 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,191 reviews)
"Great place to stay at"
United States
Aran
The price is £114
includes taxes & fees
10 Nov - 11 Nov
Hilton Garden Inn Chicago Downtown South Loop
A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

8. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 7.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,411 reviews)
"Friendly staff, great location"
Canada
Anna
The price is £171
includes taxes & fees
30 Oct - 31 Oct
Hilton Chicago
A modern kitchen with a large window, a dining area, and a view of the sea.

9. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 7.1 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,519 reviews)
"Kids loved the pool, location was great for access to museums, and the breakfast was better than I expected!"
United States
Corinn
The price is £129
includes taxes & fees
10 Nov - 11 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

10. 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, (1,230 reviews)
"Great location!"
United States
Mario
The price is £155
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
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
6.6 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,308 reviews)
"Location was amazing. Loved the outdoor market in walking distance"
United States
Georgianna
The price is £176
includes taxes & fees
1 Nov - 2 Nov
Hyatt House Chicago/West Loop-Fulton Market
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.

12. The Hoxton, Chicago

The Hoxton, Chicago
4.0 star property
6.9 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (1,007 reviews)
"Great stay!"
United States
Jordan
The price is £201
includes taxes & fees
1 Nov - 2 Nov
The Hoxton, 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, 8.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2,731 reviews)
"Amazing place to stay"
United States
Shanequa
The price is £207
includes taxes & fees
12 Nov - 13 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby

14. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Streeterville, 8.6 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,728 reviews)
"Very Nice place to stay"
United States
Anand
The price is £103
includes taxes & fees
2 Nov - 3 Nov
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
A bar area with a long counter, bar stools, and a mirrored wall.

15. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 8.4 mi from Sleepy Hollow
8.4 out of 10, Very good, (3,982 reviews)
"Great stay"
United States
KURT
The price is £107
includes taxes & fees
9 Nov - 10 Nov
The Whitehall Hotel, BW Premier Collection
A multi-story hotel with a prominent sign reading "Crowne Plaza."

16. 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, (2,734 reviews)
"Nice hotel and location was perfect."
United States
Chriselda
The price is £152
includes taxes & fees
1 Nov - 2 Nov
Crowne Plaza Chicago West Loop by IHG
A bar area with a checkered floor, leather seating, and a bar counter with a visible liquor selection.

17. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 8 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,974 reviews)
"Hotel is great for the price."
United States
alex
The price is £122
includes taxes & fees
1 Nov - 2 Nov
ACME Hotel Chicago, Outset Collection by Hilton
An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.

18. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Theatre District, 7.5 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,716 reviews)
"Beautiful hotel with wonderful staff!"
United States
Christy
The price is £194
includes taxes & fees
31 Oct - 1 Nov
Palmer House a Hilton Hotel
A spacious lobby with a central coffee table, sofas, and a large mirror.

19. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
8.7 mi from Sleepy Hollow
8.0 out of 10, Very good, (2,497 reviews)
"Great stay, comfy beds :)"
United States
Cindy
The price is £129
includes taxes & fees
1 Nov - 2 Nov
The Chicago Hotel Collection Ambassador Gold Coast
A cozy room with a sofa, a dining table, and a window with a view of buildings.

20. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
6.8 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (338 reviews)
"Amazing place to stay would definitely come back. Felt very cozy and a home away from home 🏠"
United States
Roland
The price is £178
includes taxes & fees
15 Oct - 16 Oct
LIVN - West 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.
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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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"The property is very nice (lobby and surrounding area). The wait staff in the restaurant was incredible. The rooms weren’t all that nice - very plain."
Jessica 4-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast

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?
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?
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.

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