Hotels in Sleepy Hollow, Chicago

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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, (2,404 reviews)
"Great spot and view, would stay again!"
United States
Kimberly
The price is CA $198
CA $280 total
includes taxes & fees
Mar 24 - Mar 25
Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

The Wade
4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very good, (1,724 reviews)
"Loved this hotel, i will be back"
United States
Shari
The price is CA $177
CA $208 total
includes taxes & fees
Mar 31 - Apr 1
The Wade

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,685 reviews)
"Amazing place to stay!"
United States
Nia
The price is CA $179
CA $250 total
includes taxes & fees
Apr 1 - Apr 2
Hilton 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, (9,948 reviews)
"Great location, beautiful historic hotel with clean, updated rooms. "
United States
Jennifer
The price is CA $133
CA $156 total
includes taxes & fees
Apr 1 - Apr 2
Congress Plaza Hotel

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,042 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is CA $130
CA $152 total
includes taxes & fees
Mar 23 - Mar 24
River Hotel

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,231 reviews)
"Helpful staff, great location with views, restaurant and bar on-site"
United States
Natalie
The price is CA $167
CA $244 total
includes taxes & fees
Mar 29 - Mar 30
Swissotel - Chicago

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, (2,695 reviews)
"Perfect location!!"
United States
Kelly
The price is CA $131
CA $153 total
includes taxes & fees
Mar 24 - Mar 25
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, (2,035 reviews)
"Great hotel in a great location."
United States
Ben
The price is CA $134
CA $157 total
includes taxes & fees
Mar 29 - Mar 30
Central Loop Hotel

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,022 reviews)
"Nice little getaway, I really enjoyed the staff "
United States
Joshua
The price is CA $172
CA $242 total
includes taxes & fees
Mar 24 - Mar 25
Arlo Chicago

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, (496 reviews)
"Lots of stuff close by , cool vibe inside and very nice staff"
United States
Abel
The price is CA $116
CA $136 total
includes taxes & fees
Mar 24 - Mar 25
FOUND Hotel Chicago River North

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, (3,779 reviews)
"Amazing hotel-- Loved staying here."
United States
Maureen
The price is CA $210
CA $247 total
includes taxes & fees
Mar 24 - Mar 25
L7 Chicago by LOTTE

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.0 out of 10, Very good, (2,804 reviews)
"Great location, clean and decent sized room, staff was helpful and amenities are very convenient!"
United States
MaryJane
The price is CA $94
CA $135 total
includes taxes & fees
Mar 30 - Mar 31
Freehand Chicago

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, (2,328 reviews)
"Good stay! Great staff! "
United States
Ruchi
The price is CA $184
CA $251 total
includes taxes & fees
Apr 5 - Apr 6
Palmer House a Hilton Hotel

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, (1,910 reviews)
"Staff was friendly, valet parking is quick and the attached restaurant is very good."
United States
Codi
The price is CA $162
CA $190 total
includes taxes & fees
Apr 13 - Apr 14
Hilton Garden Inn Chicago Downtown South Loop

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,122 reviews)
"Prefect location to walk to everything we wanted & the staff was great!"
United States
Michael
The price is CA $130
CA $152 total
includes taxes & fees
Mar 19 - Mar 20
Club Quarters Hotel Wacker at Michigan, Chicago

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, (3,147 reviews)
"Clean rooms friendly staff, great location "
United States
Roxana
The price is CA $148
CA $174 total
includes taxes & fees
Mar 22 - Mar 23
Aloft Chicago Mag Mile

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, (1,314 reviews)
"Great hotel with great location. Would definitely stay here again. "
United States
Sheila
The price is CA $165
CA $194 total
includes taxes & fees
Mar 23 - Mar 24
The Chicago Hotel Collection Ambassador Gold Coast

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, (3,421 reviews)
"The staff was very helpful with the check in and the room was great. "
United States
George
The price is CA $132
CA $155 total
includes taxes & fees
Mar 31 - Apr 1
Club Quarters Hotel, Central Loop, Chicago

Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,008 reviews)
"Clean rooms, lots to check out near by"
United States
Kassia
The price is CA $133
CA $180 total
includes taxes & fees
Apr 12 - Apr 13
Le Méridien Essex Chicago

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.5 km from Sleepy Hollow
7.6 out of 10, Good, (1,237 reviews)
"Amazing stay "
United States
Napoleon
The price is CA $165
CA $194 total
includes taxes & fees
Mar 18 - Mar 19
The Chicago Hotel Collection - 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.

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 family hotels in Sleepy Hollow?
The Carlton Inn Midway in Chicago is a fantastic option for families seeking comfort and convenience during their travels. This family-friendly hotel offers complimentary cribs and free stays for children, making it an excellent choice for those traveling with little ones.
What hotels in Sleepy Hollow offer free breakfast?
Carlton Inn Midway in Chicago is an excellent choice for travellers seeking a family-friendly atmosphere with convenient amenities. This welcoming hotel offers a complimentary continental breakfast, ensuring that families can start their day off right without any hassle. The 24-hour airport shuttle service makes it easy for guests to navigate their travel plans, great for families arriving with little ones in tow.
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?
Before booking your Sleepy Hollow hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia.
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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