Default HTG hotel image

Search Hotels in Sleepy Hollow, Chicago

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Filter by

Star rating

Guest rating

Selecting then applying a filter from this group will update the results on a new page

Our top choices for Sleepy Hollow hotels

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

1. 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, (10,199 reviews)
"Lovely stay, beautiful architecture"
United States
Mia
The price is £94
includes taxes & fees
8 Sept - 9 Sept
Congress Plaza Hotel
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.

2. 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, (2,658 reviews)
The price is £176
includes taxes & fees
7 Sept - 8 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
A modern interior with a bar area, seating, and decorative wooden panels.

3. 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, (2,740 reviews)
"Very good hotel"
United States
Diego
The price is £122
includes taxes & fees
1 Sept - 2 Sept
Best Western Grant Park Hotel
A marble-floored lobby with double doors and elevators, each marked with a 'CQ' sign.

4. River Hotel

River Hotel
4.0 star property
The Loop, 7.9 mi from Sleepy Hollow
8.8 out of 10, Excellent, (5,391 reviews)
"The location was perfect, and the staff was extremely helpful"
United States
Patti
The price is £114
includes taxes & fees
8 Sept - 9 Sept
River Hotel
A large, multi-story hotel with a prominent entrance and classical architectural details.

5. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 7.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (3,088 reviews)
"Very nice place would stay again"
United States
Konner
The price is £169
includes taxes & fees
8 Sept - 9 Sept
Hilton Chicago

6. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 7.2 mi from Sleepy Hollow
9.6 out of 10, Exceptional, (1,274 reviews)
"The staff were really nice and friendly. Our room was nice and clean. I would stay here again!"
United States
Melanie
The price is £159
includes taxes & fees
1 Sept - 2 Sept
Hilton Vacation Club Hotel Blake Chicago
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

7. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 7.1 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,133 reviews)
"Great stay"
United States
Dhannetta
The price is £134
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Chicago Downtown South Loop
A spacious lobby with a central coffee table, sofas, and a large mirror.

8. 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
8.0 out of 10, Very good, (2,113 reviews)
"Good place to stay"
United States
Alma
The price is £125
includes taxes & fees
31 Aug - 1 Sept
The Chicago Hotel Collection Ambassador Gold Coast
A cozy room with a sofa, a dining table, and a window with a view of buildings.

9. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
6.8 mi from Sleepy Hollow
9.4 out of 10, Exceptional, (235 reviews)
"Clean room, nice staff, cool vibe. Enjoyed my stay!!"
United States
Courtney
The price is £111
includes taxes & fees
31 Aug - 1 Sept
LIVN - West Loop Chicago
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

10. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 7.3 mi from Sleepy Hollow
8.8 out of 10, Excellent, (3,623 reviews)
"Greta stay and location"
Canada
Youssef
The price is £116
includes taxes & fees
30 Aug - 31 Aug
Club Quarters Hotel, Central Loop, Chicago
The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

11. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 8.6 mi from Sleepy Hollow
9.0 out of 10, Wonderful, (1,449 reviews)
"Nice upscale hotel in a great area."
United States
Christie
The price is £114
includes taxes & fees
8 Sept - 9 Sept
Claridge House Chicago, Tapestry Collection by Hilton
A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

12. 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, (1,000 reviews)
"great location"
United States
Karaline
The price is £108
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
A modern kitchen with a large window, a dining area, and a view of the sea.

13. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 7.1 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,438 reviews)
"Clean, friendly staff, quick valet, and a decent breakfast"
United States
AMBER
The price is £141
includes taxes & fees
7 Sept - 8 Sept
Homewood Suites by Hilton Chicago Downtown South Loop
A hotel with a modern design, featuring a prominent curved glass facade and multiple floors.

14. 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, (2,971 reviews)
"Excellent location"
United States
Rajiv
The price is £161
includes taxes & fees
1 Sept - 2 Sept
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
A cityscape at dusk with high-rise buildings, including a Hilton hotel.

15. 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, (4,857 reviews)
"Great location very nice rooms"
United States
susie
The price is £139
includes taxes & fees
1 Sept - 2 Sept
Hilton Chicago/Magnificent Mile Suites
A grand staircase in a hotel lobby with marble walls, a patterned carpet, and seating areas with blue and brown upholstered chairs.

16. Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 7.9 mi from Sleepy Hollow
8.8 out of 10, Excellent, (2,401 reviews)
"The staff was awesome and location was superb!!"
United States
Daphnie
The price is £125
includes taxes & fees
8 Sept - 9 Sept
Club Quarters Hotel Wacker at Michigan, Chicago
A hotel lobby with a bar area, seating, and a large mirror.

17. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 7.1 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (1,398 reviews)
"Very clean, front desk staff were extremely friendly and welcoming. Beds were the most comfortable we have ever slept in when traveling!"
United States
Theresa
The price is £149
includes taxes & fees
7 Sept - 8 Sept
Hilton Garden Inn Chicago Central Loop
A couple sitting on a blue couch with a table in front of them, holding drinks and a pizza.

18. 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, (2,153 reviews)
"Room, staff, was great!"
United States
Jesse
The price is £100
includes taxes & fees
8 Sept - 9 Sept
Hotel Saint Clair- Magnificent Mile
A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

19. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 7.6 mi from Sleepy Hollow
9.2 out of 10, Wonderful, (2,361 reviews)
"Great location."
United States
Xiao
The price is £141
includes taxes & fees
7 Sept - 8 Sept
Silversmith Hotel Chicago Downtown
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.

20. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 7.3 mi from Sleepy Hollow
8.6 out of 10, Excellent, (2,287 reviews)
"Great location."
United States
Yiyang
The price is £109
includes taxes & fees
30 Aug - 31 Aug
Central Loop 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.
View all properties

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 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 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 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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

8/10 Good
"Excellent location and staff was friendly and very helpful. Elevators made funny noises though. Kinda scary. Still recommend."
Rhonda 2-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 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.

Explore a world of travel with Expedia