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Check prices for these dates

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

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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, (2,513 reviews)
"I loved it here and will definitely stay again."
United States
Gina
The price is £214
includes taxes & fees
26 May - 27 May
Sable at Navy Pier Chicago, Curio Collection by Hilton
Room service – dining

The Wade

The Wade
4.5 star property
Streeterville, 8.6 mi from Sleepy Hollow
8.4 out of 10, Very good, (1,843 reviews)
"Excellent location, clean modern rooms."
United States
Molly
The price is £127
includes taxes & fees
26 May - 27 May
The Wade
2 bars/lounges

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 8.2 mi from Sleepy Hollow
8.6 out of 10, Excellent, (1,636 reviews)
"Beautiful views"
United States
Dominique
The price is £289
includes taxes & fees
14 Jun - 15 Jun
Sheraton Grand Chicago Riverwalk
Indoor wedding

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
8.1 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (3,345 reviews)
"Great location!"
United States
Maria
The price is £210
includes taxes & fees
27 May - 28 May
Swissotel - Chicago
Outdoor pool, pool cabanas (surcharge), pool umbrellas

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, (2,488 reviews)
"This is a beautiful hotel and the location was perfect."
United States
Felisha
The price is £150
includes taxes & fees
26 May - 27 May
DoubleTree by Hilton Chicago - Magnificent Mile
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, (2,856 reviews)
"Breakfast was excellent."
United States
Janine
The price is £163
includes taxes & fees
26 May - 27 May
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
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, (1,945 reviews)
"Great Hotel "
United States
Dylan
The price is £226
includes taxes & fees
26 May - 27 May
Radisson Blu Aqua Hotel 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, (2,168 reviews)
"Great place"
United States
JOSE
The price is £216
includes taxes & fees
26 May - 27 May
Fairmont Chicago at Millennium Park
Lobby

Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,251 reviews)
"Nice place to stay"
United States
Jimmie
The price is £199
includes taxes & fees
14 Jun - 15 Jun
Aloft by Marriott Chicago Mag Mile
Bar (on property)

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.8 out of 10, Excellent, (1,274 reviews)
"Happy with our stay!"
United States
Jennifer
The price is £133
includes taxes & fees
26 May - 27 May
Ivy Boutique Hotel
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, (2,478 reviews)
"Perfect location, very comfortable rooms, friendly staff."
United States
Annabelle
The price is £144
includes taxes & fees
26 May - 27 May
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
View from property

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,002 reviews)
"All around great stay. "
United States
Nicholas
The price is £132
includes taxes & fees
26 May - 27 May
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Exterior

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 8.6 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (4,341 reviews)
"Beautiful Hotel great location"
United States
Nereida
The price is £167
includes taxes & fees
27 May - 28 May
Hilton Chicago/Magnificent Mile Suites
Shopping centre

Millennium Hotel Knickerbocker Chicago

Millennium Hotel Knickerbocker Chicago
4.0 star property
Streeterville, 8.6 mi from Sleepy Hollow
8.6 out of 10, Excellent, (1,979 reviews)
"Loved everything including location and food options. Great hotel. "
United States
Eileen
The price is £145
includes taxes & fees
26 May - 27 May
Millennium Hotel Knickerbocker Chicago
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, (3,499 reviews)
"Very good place to stay. I really liked the lobby — it’s very spacious. The lobby design is also very open and artistic."
Canada
Tong
The price is £234
includes taxes & fees
26 May - 27 May
Hyatt Regency Chicago
Exterior

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,096 reviews)
"Great stay!"
United States
Milo
The price is £198
includes taxes & fees
26 May - 27 May
Hyatt Centric Chicago Magnificent Mile
Premium bedding, in-room safe, desk, blackout curtains

Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 8.2 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,906 reviews)
"Great Place to stay while in Chicago."
United States
Stacy
The price is £157
includes taxes & fees
26 May - 27 May
Courtyard by Marriott Chicago Magnificent Mile
Exterior

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 8.4 mi from Sleepy Hollow
7.8 out of 10, Good, (1,472 reviews)
"Great stay"
United States
Ontario
The price is £107
includes taxes & fees
27 May - 28 May
The Chicago Hotel Collection - Magnificent Mile
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, (4,245 reviews)
"Great location & breakfast was amazing."
United States
sierra
The price is £233
includes taxes & fees
16 Jun - 17 Jun
Hotel Riu Plaza Chicago
Lobby

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 7.4 mi from Sleepy Hollow
8.0 out of 10, Very good, (10,140 reviews)
"Excellent stay"
United States
Jennifer
The price is £118
includes taxes & fees
27 May - 28 May
Congress Plaza Hotel
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.

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.

Panoramic view of Lincoln Park and the Chicago skyline.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Sleepy Hollow Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"."
Feliberto Bazan 4-night trip
Posted less than an hour ago
Hilton Chicago

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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