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This weekend
19 Jun - 21 Jun
Next weekend
26 Jun - 28 Jun

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Our top choices for Sleepy Hollow hotels

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, (2,291 reviews)
"Would definitely stay there again"
United States
Benjy
The price is £139
includes taxes & fees
1 Jul - 2 Jul
The Godfrey Hotel Chicago
Exterior

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
River North, 7.4 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,397 reviews)
"A great stay!"
United States
Tammie
The price is £158
includes taxes & fees
1 Jul - 2 Jul
Holiday Inn Chicago Dwtn - The Mart by IHG
Exterior

Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile
2.5 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.0 out of 10, Very good, (1,444 reviews)
"The staff is tops! Love this hotel!!!"
United States
Connie
The price is £195
includes taxes & fees
1 Jul - 2 Jul
Hampton Inn Chicago Downtown/Magnificent Mile
Exterior

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
3.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.2 out of 10, Very good, (1,007 reviews)
"5/5 would definitely stay again!"
United States
Ivan
The price is £175
includes taxes & fees
2 Jul - 3 Jul
Homewood Suites by Hilton Chicago Downtown/Magnificent Mile
Exterior

Arlo Chicago

Arlo Chicago
4.0 star property
Theatre District, 7.8 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (2,155 reviews)
"Excellent hotel! Will definitely stay again."
United States
Justin
The price is £128
includes taxes & fees
8 Jul - 9 Jul
Arlo 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, (10,286 reviews)
"Great stay!"
United States
Daniel
The price is £121
includes taxes & fees
29 Jun - 30 Jun
Congress Plaza Hotel
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, (4,436 reviews)
"Great stay!"
United States
Avradita
The price is £124
includes taxes & fees
30 Jun - 1 Jul
Hilton Chicago/Magnificent Mile Suites
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, (1,611 reviews)
"Very good location, breakfast is fantastic, dinner and bar are great."
United States
Zhiwen
The price is £136
includes taxes & fees
30 Jun - 1 Jul
The Chicago Hotel Collection Ambassador Gold Coast
Lobby

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 7.3 mi from Sleepy Hollow
7.4 out of 10, Good, (2,650 reviews)
"Great location and helpful staff."
United States
Ming
The price is £118
includes taxes & fees
30 Jun - 1 Jul
Travelodge by Wyndham Downtown Chicago
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, (4,461 reviews)
"Clean room, great breakfast and close to everything we needed"
United States
Kyle
The price is £163
includes taxes & fees
6 Jul - 7 Jul
Hotel Riu Plaza Chicago
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, (1,811 reviews)
"All around great property and a wonderful location"
United States
Bruce
The price is £159
includes taxes & fees
2 Jul - 3 Jul
Omni Chicago 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, (2,260 reviews)
"Wonderful stay"
United States
Taylor
The price is £144
includes taxes & fees
7 Jul - 8 Jul
Silversmith Hotel Chicago Downtown
Presidential Suite, 1 Bedroom, Non Smoking | Premium bedding, in-room safe, desk, blackout curtains

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown
4.0 star property
River North, 8.1 mi from Sleepy Hollow
8.8 out of 10, Excellent, (1,599 reviews)
"Great stay"
United States
Matt
The price is £147
includes taxes & fees
1 Jul - 2 Jul
Hotel 55 Chicago Downtown
Exterior

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 7.2 mi from Sleepy Hollow
9.6 out of 10, Exceptional, (1,258 reviews)
"The best place I’ve stayed in Chicago"
United States
Robyn
The price is £141
includes taxes & fees
7 Jul - 8 Jul
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
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, (3,745 reviews)
"Great location!"
United States
William
The price is £227
includes taxes & fees
30 Jun - 1 Jul
LondonHouse Chicago, Curio Collection by Hilton
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, (2,736 reviews)
"Nice place to stay at"
United States
Tammy
The price is £106
includes taxes & fees
1 Jul - 2 Jul
Best Western Grant Park Hotel
Exterior

Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 7.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,879 reviews)
"Great stay"
United States
Jose saul
The price is £196
includes taxes & fees
30 Jun - 1 Jul
Hilton Chicago
Exterior

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Streeterville, 8.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,070 reviews)
"Great location, historic charm, friendly and helpful staff."
United States
Peter Anthony
The price is £140
includes taxes & fees
2 Jul - 3 Jul
Warwick Allerton - Chicago
Bar (on property)

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 8.4 mi from Sleepy Hollow
8.4 out of 10, Very good, (3,950 reviews)
"Great location, comfortable rooms, nice breakfast."
United States
Luis
The price is £120
includes taxes & fees
30 Jun - 1 Jul
The Whitehall Hotel, BW Premier Collection
Cocktail bar

Freehand Chicago

Freehand Chicago
4.0 star property
River North, 8 mi from Sleepy Hollow
8.0 out of 10, Very good, (3,120 reviews)
"It was good place to stay for the Go Fest Event"
United States
Ken
The price is £138
includes taxes & fees
5 Jul - 6 Jul
Freehand Chicago
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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"The room was clean and it was nice having a balcony. It was a little busy because Prom was happening but not too terribly bad. Would stay again. Beds comfortable."
Kristen 1-night trip
Posted 1 hour ago
Hyatt Regency O'Hare 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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