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

Next weekend
In two weeks

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Sleepy Hollow hotels

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, (2,482 reviews)
"Great place to stay "
United States
Mark
The price is CA $249
CA $343 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,770 reviews)
"Clean room and great location "
United States
Diana
The price is CA $216
CA $297 total
includes taxes & fees
May 25 - May 26
Hilton Chicago

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, (4,034 reviews)
"It was great property, amazing location and the breakfast was fantastic. "
United States
Nichole
The price is CA $183
CA $256 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza Chicago

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, (1,976 reviews)
"Had a great stay-5 stars of 5"
United States
donald
The price is CA $178
CA $212 total
includes taxes & fees
May 26 - May 27
Hilton Garden Inn Chicago Downtown South Loop

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (4,002 reviews)
"Clean hotel great restaurant "
United States
ELIZABETH
The price is CA $196
CA $234 total
includes taxes & fees
May 25 - May 26
L7 Chicago by LOTTE

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, (10,134 reviews)
"Great stay"
United States
Matthew
The price is CA $170
CA $202 total
includes taxes & fees
May 8 - May 9
Congress Plaza Hotel

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,939 reviews)
"Great stay"
United States
Agnes Nmabila
The price is CA $133
CA $182 total
includes taxes & fees
May 25 - May 26
Freehand Chicago

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, (2,244 reviews)
"This was a great hotel. The staff and accommodations were terrific. I really enjoyed my stay "
United States
Alex
The price is CA $162
CA $234 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown

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, (1,056 reviews)
"Wonderful restaurant, amazing food."
United States
Robert
The price is CA $181
CA $255 total
includes taxes & fees
May 25 - May 26
Staypineapple, An Iconic Hotel, The Loop

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,296 reviews)
"Very good, would stay here again!"
United States
Lorena
The price is CA $269
CA $368 total
includes taxes & fees
May 27 - May 28
Swissotel - Chicago

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, (3,682 reviews)
"Loved staying at this hotel"
United States
Kimberly Marie
The price is CA $245
CA $331 total
includes taxes & fees
May 26 - May 27
LondonHouse Chicago, Curio Collection by Hilton

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, (2,428 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is CA $201
CA $279 total
includes taxes & fees
May 25 - May 26
Palmer House a Hilton Hotel

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, (580 reviews)
"Great location great staff great hotel!"
United States
Refak
The price is CA $121
CA $142 total
includes taxes & fees
May 26 - May 27
FOUND Hotel Chicago River North

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, (2,574 reviews)
"Perfect location for a good price that aside, mid hotel "
United States
Nicolas Esteban
The price is CA $143
CA $170 total
includes taxes & fees
May 27 - May 28
Travelodge by Wyndham Downtown Chicago

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,156 reviews)
"Excellent location, very clean room and friendly staff"
United States
Alejandra
The price is CA $184
CA $218 total
includes taxes & fees
May 26 - May 27
River Hotel

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, (2,688 reviews)
"Great location, right across the street from the park."
United States
Jamison
The price is CA $158
CA $188 total
includes taxes & fees
May 25 - May 26
Best Western Grant Park Hotel

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,104 reviews)
"Clean rooms and very good location. "
Canada
Rudra
The price is CA $127
CA $150 total
includes taxes & fees
May 25 - May 26
Central Loop Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 11.6 km from Sleepy Hollow
8.4 out of 10, Very good, (1,007 reviews)
"A fantastic hotel for solo travelers - perfect area, close to museums and restaurants, great bar"
United States
Michelle Renee
The price is CA $202
CA $241 total
includes taxes & fees
May 8 - May 9
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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, (1,363 reviews)
"It was in a great location near everything. "
United States
Dwight Demond
The price is CA $168
CA $200 total
includes taxes & fees
May 9 - May 10
The Chicago Hotel Collection - Magnificent Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,218 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is CA $202
CA $241 total
includes taxes & fees
May 10 - May 11
Aloft Chicago Mag 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.

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 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 24-48 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 Sleepy Hollow hotel booking with Expedia?
With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Sleepy Hollow hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.
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.

Explore a world of travel with Expedia