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Check prices for these dates

This weekend
17 Jul - 19 Jul
Next weekend
24 Jul - 26 Jul

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Our top choices for Sleepy Hollow hotels

Restaurant

FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott
3.0 star property
River North, 7.8 mi from Sleepy Hollow
6.8 out of 10, (11 reviews)
"Overall was a good stay!! Wish the place next door wasn’t as loud at night."
United States
Lia
The price is £145
includes taxes & fees
26 Jul - 27 Jul
FOUND Hotels, Chicago, Series by Marriott
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 8 mi from Sleepy Hollow
7.8 out of 10, Good, (3,196 reviews)
"Great location."
United States
Clifton
The price is £128
includes taxes & fees
10 Aug - 11 Aug
Freehand Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 7.3 mi from Sleepy Hollow
7.6 out of 10, Good, (2,707 reviews)
"Excellent hotel and services"
United Kingdom
Marobe
The price is £152
includes taxes & fees
10 Aug - 11 Aug
Travelodge by Wyndham Downtown Chicago
Superior Apartment, 2 Bedrooms, Kitchen | Living area | LED TV, Netflix, Hulu, streaming services

LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
6.8 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (167 reviews)
"Clean, new, and cozy stay in a great location."
United States
Pedro
The price is £143
includes taxes & fees
19 Jul - 20 Jul
LIVN - West Loop Chicago
Lobby

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 8.7 mi from Sleepy Hollow
8.2 out of 10, Very good, (1,747 reviews)
"Nice place to stay"
Australia
Anna
The price is £146
includes taxes & fees
27 Jul - 28 Jul
The Chicago Hotel Collection Ambassador Gold Coast
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, (10,261 reviews)
"We’ve stayed there twice and probably will again."
United States
Ashley
The price is £168
includes taxes & fees
12 Aug - 13 Aug
Congress Plaza Hotel
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, (1,747 reviews)
"Nice and comfortable place to stay"
Australia
Precious
The price is £138
includes taxes & fees
27 Jul - 28 Jul
The Chicago Hotel Collection - 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, (2,529 reviews)
"Staff was very nice. Hotel is beautiful "
United States
Britney Q
The price is £215
includes taxes & fees
9 Aug - 10 Aug
Palmer House a Hilton Hotel
Lobby

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 7.6 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2,299 reviews)
"Wonderful stay"
United States
Taylor
The price is £165
includes taxes & fees
9 Aug - 10 Aug
Silversmith Hotel Chicago Downtown
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,033 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is £146
includes taxes & fees
9 Aug - 10 Aug
Warwick Allerton - Chicago
Room service – dining

The Wade

The Wade
4.5 star property
Streeterville, 8.6 mi from Sleepy Hollow
8.6 out of 10, Excellent, (1,925 reviews)
"Great stay and friendly staff!"
Canada
Richard
The price is £189
includes taxes & fees
19 Jul - 20 Jul
The Wade
Rooftop bar, al fresco dining, open daily

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 8 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,332 reviews)
"I liked the ambiance of the hotel, everyone was nice and it was very clean."
United States
Tanil
The price is £168
includes taxes & fees
9 Aug - 10 Aug
The Godfrey Hotel Chicago
Interior detail

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop
4.0 star property
Theatre District, 7.6 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (1,147 reviews)
"Beautiful historic building; dog friendly!"
United States
Zoe
The price is £208
includes taxes & fees
9 Aug - 10 Aug
Staypineapple, An Iconic Hotel, The Loop
Reception hall

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 8.1 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (3,741 reviews)
"Nice place great staff and a great location"
United States
Byron
The price is £178
includes taxes & fees
27 Jul - 28 Jul
Eurostars Magnificent Mile
2 restaurants; breakfast, lunch and dinner served

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, (3,803 reviews)
"Beautiful hotel and location. Staff were very friendly and kind."
Canada
Sophie
The price is £222
includes taxes & fees
9 Aug - 10 Aug
LondonHouse Chicago, Curio Collection by Hilton
Lobby sitting area

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 8.2 mi from Sleepy Hollow
8.4 out of 10, Very good, (2,037 reviews)
"It was convenient, very close to a lot of restaurants and shops."
United States
Rocio
The price is £146
includes taxes & fees
19 Jul - 20 Jul
Hotel Saint Clair- Magnificent Mile
Restaurant

Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 7.1 mi from Sleepy Hollow
8.2 out of 10, Very good, (2,753 reviews)
"Nice place to stay at"
United States
Tammy
The price is £144
includes taxes & fees
9 Aug - 10 Aug
Best Western Grant Park 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.
A busy city street with tall buildings, a bus, and cars.

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.

A historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

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

A river with yellow boats, a bridge, and tall buildings.

The Loop

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

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

A river with a city skyline in the background, surrounded by green trees and grass.

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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Hotel was super close to everything especially Cloud Gate and easily walkable areas. A little older hotel but the rooms were historic and nice and we loved our view and cannot wait to visit Chicago again!"
Madelin 2-night trip
Posted less than an hour ago
Congress Plaza Hotel

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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