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Hotels in Sleepy Hollow, Chicago

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Our top choices for Sleepy Hollow hotels

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 12.8 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,296 reviews)
"Would definitely stay there again"
United States
Benjy
The price is CA $188
CA $255 total
includes taxes & fees
Jul 1 - Jul 2
The Godfrey Hotel Chicago

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
River North, 11.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,404 reviews)
"A great stay!"
United States
Tammie
The price is CA $249
CA $296 total
includes taxes & fees
Jul 1 - Jul 2
Holiday Inn Chicago Dwtn - The Mart by IHG

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Streeterville, 13.4 km from Sleepy Hollow
8.0 out of 10, Very good, (1,445 reviews)
"The staff is tops! Love this hotel!!!"
United States
Connie
The price is CA $308
CA $366 total
includes taxes & fees
Jul 1 - Jul 2
Hampton Inn Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.2 out of 10, Very good, (1,009 reviews)
"5/5 would definitely stay again!"
United States
Ivan
The price is CA $276
CA $328 total
includes taxes & fees
Jul 2 - Jul 3
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,122 reviews)
"Excellent hotel! Will definitely stay again."
United States
Justin
The price is CA $279
CA $374 total
includes taxes & fees
Jul 5 - Jul 6
Arlo Chicago

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, (10,295 reviews)
"Great stay!"
United States
Daniel
The price is CA $191
CA $227 total
includes taxes & fees
Jun 29 - Jun 30
Congress Plaza Hotel

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, (4,437 reviews)
"Great stay!"
United States
Avradita
The price is CA $195
CA $232 total
includes taxes & fees
Jul 1 - Jul 2
Hilton Chicago/Magnificent Mile Suites

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, (1,607 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is CA $215
CA $256 total
includes taxes & fees
Jul 1 - Jul 2
The Chicago Hotel Collection Ambassador Gold Coast

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 11.8 km from Sleepy Hollow
7.6 out of 10, Good, (2,601 reviews)
"Great location and helpful staff."
United States
Ming
The price is CA $177
CA $211 total
includes taxes & fees
Jul 5 - Jul 6
Travelodge by Wyndham Downtown 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, (4,471 reviews)
The price is CA $224
CA $306 total
includes taxes & fees
Jul 5 - Jul 6
Hotel Riu Plaza Chicago

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 13.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,814 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is CA $214
CA $301 total
includes taxes & fees
Jul 5 - Jul 6
Omni Chicago Hotel

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, (2,254 reviews)
"Wonderful stay"
United States
Taylor
The price is CA $171
CA $246 total
includes taxes & fees
Jul 5 - Jul 6
Silversmith Hotel Chicago Downtown

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, (1,570 reviews)
"Great stay"
United States
Matt
The price is CA $197
CA $276 total
includes taxes & fees
Jul 1 - Jul 2
Hotel 55 Chicago Downtown

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,250 reviews)
"The best place I’ve stayed in Chicago"
United States
Robyn
The price is CA $237
CA $281 total
includes taxes & fees
Jul 5 - Jul 6
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

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, (3,738 reviews)
"Great location!"
United States
William
The price is CA $332
CA $435 total
includes taxes & fees
Jul 1 - Jul 2
LondonHouse Chicago, Curio Collection by Hilton

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, (2,710 reviews)
"Nice place to stay at"
United States
Tammy
The price is CA $167
CA $198 total
includes taxes & fees
Jul 1 - Jul 2
Best Western Grant Park Hotel

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,863 reviews)
"Great stay"
United States
Jose saul
The price is CA $274
CA $367 total
includes taxes & fees
Jul 1 - Jul 2
Hilton Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,008 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is CA $164
CA $236 total
includes taxes & fees
Jul 2 - Jul 3
Warwick Allerton - Chicago

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.5 km from Sleepy Hollow
8.4 out of 10, Very good, (3,927 reviews)
The price is CA $189
CA $225 total
includes taxes & fees
Jun 30 - Jul 1
The Whitehall Hotel, BW Premier Collection

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (3,128 reviews)
"It was good place to stay for the Go Fest Event"
United States
Ken
The price is CA $167
CA $265 total
includes taxes & fees
Jul 5 - Jul 6
Freehand 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.

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.

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