Hotels in Sleepy Hollow, Chicago from CA $135

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Our top choices for Sleepy Hollow hotels

1. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
10.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,308 reviews)
"Loved the continental breakfast and how close different bars and restaurants were at :)"
United States
Carole
The price is CA $162
CA $193 total
includes taxes & fees
Nov 22 - Nov 23
Hyatt House Chicago/West Loop-Fulton Market

2. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,525 reviews)
"Enjoyed my stay will book again!"
United States
Jordan
The price is CA $151
CA $221 total
includes taxes & fees
Nov 27 - Nov 28
Hilton Chicago

3. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,193 reviews)
"Great place to stay at"
United States
Aran
The price is CA $135
CA $161 total
includes taxes & fees
Nov 23 - Nov 24
Hilton Garden Inn Chicago Downtown South Loop

4. Best Western Grant Park Hotel

Best Western Grant Park Hotel
2.5 star property
The Loop, 11.5 km from Sleepy Hollow
8.2 out of 10, Very good, (2,736 reviews)
"Room was dated but clean, staff was friendly, location was perfect for my needs"
United States
Michelle
The price is CA $137
CA $163 total
includes taxes & fees
Nov 23 - Nov 24
Best Western Grant Park Hotel

5. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,530 reviews)
"Wonderful room and great breakfast buffet!"
United States
Nicole
The price is CA $147
CA $175 total
includes taxes & fees
Nov 23 - Nov 24
Homewood Suites by Hilton Chicago Downtown South Loop

6. Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
West Loop, 10.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,268 reviews)
"good breakfast, friendly staff"
United States
Donna
The price is CA $141
CA $185 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn & Suites Chicago - Downtown by IHG

7. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Streeterville, 14.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,764 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is CA $183
CA $266 total
includes taxes & fees
Nov 23 - Nov 24
Sable at Navy Pier Chicago, Curio Collection by Hilton

8. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,789 reviews)
"Nice hotel and location was perfect."
United States
Chriselda
The price is CA $189
CA $224 total
includes taxes & fees
Nov 25 - Nov 26
Crowne Plaza Chicago West Loop by IHG

9. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,689 reviews)
"Great location and the front desk staff was exceptional - Addy, Julian and the whole crew on Thursday and Friday morning!"
United States
maribeth
The price is CA $165
CA $196 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Place Chicago/Downtown - The Loop

10. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
10.9 km from Sleepy Hollow
9.2 out of 10, Wonderful, (396 reviews)
"It was a fantastic stay!"
United States
Elzbieta
The price is CA $146
CA $172 total
includes taxes & fees
Nov 11 - Nov 12
LIVN - West Loop Chicago

11. Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0 star property
River North, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,000 reviews)
"Everything was great and comfortable will stay again"
United States
Safrona
The price is CA $108
CA $170 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Chicago Downtown, Autograph Collection by Marriott

12. Le Méridien Essex Chicago

Le Méridien Essex Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,000 reviews)
"Fantastic location and facility. Comfortable bed and nice shower! Perfect hotel for the Bears Game!"
United States
Taso
The price is CA $166
CA $223 total
includes taxes & fees
Nov 26 - Nov 27
Le Méridien Essex Chicago

13. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,442 reviews)
"Will definitely stay again!!"
United States
Jasmine
The price is CA $189
CA $225 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Chicago Central Loop

14. Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,711 reviews)
"Great room - spacious, clean"
United States
Toninette
The price is CA $149
CA $177 total
includes taxes & fees
Nov 23 - Nov 24
Cambria Hotel Chicago Loop - Theatre District

15. Hampton Inn Majestic Chicago Theatre District

Hampton Inn Majestic Chicago Theatre District
3.0 star property
Theatre District, 12 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,001 reviews)
"we liked our stay here"
United States
Michael
The price is CA $159
CA $189 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Majestic Chicago Theatre District

16. ACME Hotel Chicago, Outset Collection by Hilton

ACME Hotel Chicago, Outset Collection by Hilton
3.5 star property
River North, 12.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,957 reviews)
"Hotel is great for the price."
United States
alex
The price is CA $126
CA $150 total
includes taxes & fees
Dec 6 - Dec 7
ACME Hotel Chicago, Outset Collection by Hilton

17. Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
The Loop, 11.9 km from Sleepy Hollow
8.0 out of 10, Very good, (10,101 reviews)
"It was a wonderful stay!"
United States
Ashya
The price is CA $162
CA $193 total
includes taxes & fees
Nov 22 - Nov 23
Congress Plaza Hotel

18. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Theatre District, 11.6 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,002 reviews)
"All the personal was very nice and helpful, the place is very clean and beautiful"
United States
Elizabeth
The price is CA $166
CA $198 total
includes taxes & fees
Dec 3 - Dec 4
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

19. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,216 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is CA $224
CA $266 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Vacation Club Hotel Blake Chicago

20. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,577 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is CA $141
CA $168 total
includes taxes & fees
Nov 22 - Nov 23
DoubleTree by Hilton Chicago - 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.

Compare top hotels in Sleepy Hollow

3.5 star property
10.6 km from Sleepy Hollow
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
2.5 star property
The Loop, 11.5 km from Sleepy Hollow
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
9.0
Wonderful
1,308 reviews
8.6
Excellent
3,525 reviews
8.8
Excellent
2,193 reviews
8.2
Very good
2,736 reviews
8.8
Excellent
2,530 reviews
The price is CA $162
CA $193 total
includes taxes & fees
Nov 22 - Nov 23
The price is CA $151
CA $221 total
includes taxes & fees
Nov 27 - Nov 28
The price is CA $135
CA $161 total
includes taxes & fees
Nov 23 - Nov 24
The price is CA $137
CA $163 total
includes taxes & fees
Nov 23 - Nov 24
The price is CA $147
CA $175 total
includes taxes & fees
Nov 23 - Nov 24
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • No WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • No Pool
  • No Spa
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods 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

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Top Sleepy Hollow Hotel Reviews

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?

Many Expedia hotel reservations are refundable, provided that you cancel before the hotel’s cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Sleepy Hollow hotel for you.

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 from CA $135 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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