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Check prices for these dates

Tonight
10 Apr - 11 Apr
Tomorrow
11 Apr - 12 Apr
This weekend
10 Apr - 12 Apr
Next weekend
17 Apr - 19 Apr

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Our top choices for Sleepy Hollow hotels

Terrace/patio

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, (2,452 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 £226
includes taxes & fees
16 Apr - 17 Apr
Sable at Navy Pier Chicago, Curio Collection by Hilton
2 bars/lounges

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 8 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (3,489 reviews)
"Increíble hotel súper friendly staff! "
United States
Alejandra
The price is £240
includes taxes & fees
9 May - 10 May
Hyatt Regency Chicago
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
8.1 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (3,250 reviews)
"Excellent stay."
United States
Fenton
The price is £238
includes taxes & fees
8 May - 9 May
Swissotel - Chicago
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 7.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,722 reviews)
"We love staying here "
United States
Carrie
The price is £196
includes taxes & fees
8 May - 9 May
Hilton Chicago
Executive lounge

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
The Loop, 8 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,112 reviews)
"lovely hotel "
United States
alyvia
The price is £244
includes taxes & fees
25 Apr - 26 Apr
Fairmont Chicago at Millennium Park
Lunch and dinner served

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
8 mi from Sleepy Hollow
8.6 out of 10, Excellent, (1,906 reviews)
"Overall a great stay."
United States
Joshua
The price is £211
includes taxes & fees
9 May - 10 May
Radisson Blu Aqua Hotel Chicago
Indoor pool

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 8.1 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (2,955 reviews)
"I love this hotel, the staff is always amazing and warm, and its perfect for a quick staycation with the family"
United States
Kinjal
The price is £189
includes taxes & fees
12 Apr - 13 Apr
InterContinental Chicago Magnificent Mile by IHG
Exterior

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.2 out of 10, Very good, (2,823 reviews)
"Every thing was in walking distance and the hotel is beautiful I will definitely be back "
United States
Shannon
The price is £160
includes taxes & fees
10 May - 11 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Lobby

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,164 reviews)
"Nice location and good hotel"
United States
Taneshia
The price is £113
includes taxes & fees
26 Apr - 27 Apr
Aloft Chicago Mag Mile
Lounge

Pendry Chicago

Pendry Chicago
4.5 star property
Theatre District, 7.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (1,137 reviews)
"Staff really friendly and hotel was clean and close to everything around the city can’t wait to come back. "
United States
Pablo Ibarra
The price is £236
includes taxes & fees
10 May - 11 May
Pendry Chicago
2 restaurants, breakfast, lunch, dinner served; American cuisine

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 7.9 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (3,648 reviews)
"One of the best hotels to stay. "
United States
Julamad
The price is £237
includes taxes & fees
7 May - 8 May
LondonHouse Chicago, Curio Collection by Hilton
Breakfast and dinner served

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Streeterville, 8.2 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (1,739 reviews)
"Great hotel"
United States
Jamal
The price is £184
includes taxes & fees
12 Apr - 13 Apr
Omni Chicago Hotel
55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 7.8 mi from Sleepy Hollow
9.6 out of 10, Exceptional, (3,892 reviews)
"Loved the stay here !"
United States
Alisha
The price is £157
includes taxes & fees
12 Apr - 13 Apr
L7 Chicago by LOTTE
Bar (on property)

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
8.3 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2,382 reviews)
"Fantastic location and a luxury hotel for a fair price."
United States
Cornelius
The price is £210
includes taxes & fees
19 Apr - 20 Apr
Sofitel Chicago Magnificent Mile
Reception

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, (2,375 reviews)
"Beautiful property, great resturant on site, an the pool and spa was amazing."
United States
Tim
The price is £158
includes taxes & fees
8 May - 9 May
Palmer House a Hilton Hotel
Terrace/patio

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,411 reviews)
"Loved this hotel!"
United States
Ellen
The price is £122
includes taxes & fees
12 Apr - 13 Apr
DoubleTree by Hilton Chicago - Magnificent Mile
Exterior

Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
7.1 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (1,002 reviews)
"Clean room and great staff"
United States
Lon
The price is £154
includes taxes & fees
30 Apr - 1 May
Hampton Inn Chicago West Loop Fulton Market Area
Lobby

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, (2,420 reviews)
"My family and I had a very good two night stay. I would stay here again."
United States
Juliette
The price is £113
includes taxes & fees
12 Apr - 13 Apr
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Front of property

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 8.2 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (3,786 reviews)
"Great hotel "
United States
Marina
The price is £134
includes taxes & fees
27 Apr - 28 Apr
Hotel Riu Plaza Chicago
Lobby lounge

Residence Inn Chicago Downtown Magnificent Mile

Residence Inn Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 8.2 mi from Sleepy Hollow
9.6 out of 10, Exceptional, (497 reviews)
"Staff was friendly and always greeted us well. "
United States
Benjamin
The price is £191
includes taxes & fees
8 May - 9 May
Residence Inn Chicago Downtown 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.
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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas 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

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

Underground passage in the Chicago O'Hare airport

O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

The Loop

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

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.

Top Sleepy Hollow Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Awesome staff! Great location "
Kathleen 3-night trip
Posted 1 hour ago
Eurostars Magnificent Mile

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 can I save on a Sleepy Hollow hotel booking with Expedia?
Members always get our best prices. Find our best Sleepy Hollow hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in 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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