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, (2,433 reviews)
"Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline. "
United States
Christopher
The price is CA $258
CA $350 total
includes taxes & fees
Apr 6 - Apr 7
Sable at Navy Pier Chicago, Curio Collection by Hilton

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, (3,156 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is CA $166
CA $194 total
includes taxes & fees
Apr 6 - Apr 7
Aloft Chicago Mag Mile

River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,049 reviews)
"very beautiful hotel and great location "
United States
Ciandra
The price is CA $152
CA $178 total
includes taxes & fees
Apr 5 - Apr 6
River Hotel

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,715 reviews)
"We love staying here "
United States
Carrie
The price is CA $291
CA $382 total
includes taxes & fees
Apr 10 - Apr 11
Hilton 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, (2,235 reviews)
"Great stay!"
United States
Jessica
The price is CA $162
CA $233 total
includes taxes & fees
Apr 9 - Apr 10
Silversmith Hotel Chicago Downtown

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, (10,007 reviews)
"The stay is well worth the affordable price."
United States
Thomas
The price is CA $150
CA $177 total
includes taxes & fees
Apr 5 - Apr 6
Congress Plaza Hotel

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 12.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,097 reviews)
"lovely hotel "
United States
alyvia
The price is CA $277
CA $374 total
includes taxes & fees
Apr 5 - Apr 6
Fairmont Chicago at Millennium Park

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, (3,711 reviews)
"Great hotel "
United States
Marina
The price is CA $180
CA $250 total
includes taxes & fees
Apr 28 - Apr 29
Hotel Riu Plaza Chicago

Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,056 reviews)
"For the price, it was a very nice a room and location. "
United States
Anna
The price is CA $129
CA $151 total
includes taxes & fees
Apr 6 - Apr 7
Central Loop Hotel

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,473 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is CA $278
CA $376 total
includes taxes & fees
Apr 5 - Apr 6
Hyatt Regency Chicago

Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,305 reviews)
"Everything was really nice!"
United States
Tristen
The price is CA $216
CA $254 total
includes taxes & fees
Apr 5 - Apr 6
Hilton Garden Inn Chicago Central Loop

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3,232 reviews)
"Excellent stay."
United States
Fenton
The price is CA $299
CA $401 total
includes taxes & fees
Apr 10 - Apr 11
Swissotel - Chicago

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, (2,148 reviews)
"Great room, lovely staff and fantastic location "
United Kingdom
Jessica
The price is CA $151
CA $178 total
includes taxes & fees
Apr 6 - Apr 7
Club Quarters Hotel Wacker at Michigan, Chicago

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, (4,039 reviews)
"Excellent stay overall"
United States
Emre
The price is CA $180
CA $211 total
includes taxes & fees
Apr 5 - Apr 6
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, (1,343 reviews)
"Very beautiful place to stay"
United States
angie
The price is CA $190
CA $223 total
includes taxes & fees
Apr 5 - Apr 6
The Chicago Hotel Collection Ambassador Gold Coast

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,365 reviews)
"Fantastic location and a luxury hotel for a fair price."
United States
Cornelius
The price is CA $249
CA $334 total
includes taxes & fees
Apr 5 - Apr 6
Sofitel Chicago Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,393 reviews)
"Loved this hotel!"
United States
Ellen
The price is CA $166
CA $194 total
includes taxes & fees
Apr 5 - Apr 6
DoubleTree by Hilton Chicago - Magnificent Mile

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
8.2 out of 10, Very good, (1,004 reviews)
"Great hotel."
United States
Kristin
The price is CA $207
CA $243 total
includes taxes & fees
Apr 4 - Apr 5
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

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, (3,416 reviews)
"Wonderful hotel, friendly and accommodating staff! "
United States
Chevon
The price is CA $145
CA $170 total
includes taxes & fees
Apr 27 - Apr 28
Club Quarters Hotel, Central Loop, Chicago

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
River North, 12.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (525 reviews)
"Love this place. Kind of like a college dorm with community kitchen. Will stay there again. "
United States
William
The price is CA $115
CA $135 total
includes taxes & fees
Apr 5 - Apr 6
FOUND Hotel Chicago River North
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.

O'Hare

Home to O'Hare International Airport, this transportation hub offers easy access to downtown via the Blue Line. The area also hosts various corporate headquarters and international consulates.

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.

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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