Hotels in Sleepy Hollow, Chicago from CA $120

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Our top choices for Sleepy Hollow hotels

1. 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, (2,742 reviews)
"Room was dated but clean, staff was friendly, location was perfect for my needs"
United States
Michelle
The price is CA $121
CA $144 total
includes taxes & fees
Dec 7 - Dec 8
Best Western Grant Park Hotel

2. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,530 reviews)
"Enjoyed my stay will book again!"
United States
Jordan
The price is CA $153
CA $223 total
includes taxes & fees
Nov 27 - Nov 28
Hilton Chicago

3. 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, (1,272 reviews)
"good breakfast, friendly staff"
United States
Donna
The price is CA $143
CA $187 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn & Suites Chicago - Downtown by IHG

4. 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, (2,196 reviews)
"Great place to stay at"
United States
Aran
The price is CA $135
CA $161 total
includes taxes & fees
Dec 9 - Dec 10
Hilton Garden Inn Chicago Downtown South Loop

5. 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, (1,311 reviews)
"Loved the continental breakfast and how close different bars and restaurants were at :)"
United States
Carole
The price is CA $207
CA $246 total
includes taxes & fees
Nov 25 - Nov 26
Hyatt House Chicago/West Loop-Fulton Market

6. 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, (2,533 reviews)
"Wonderful room and great breakfast buffet!"
United States
Nicole
The price is CA $149
CA $175 total
includes taxes & fees
Nov 23 - Nov 24
Homewood Suites by Hilton Chicago Downtown South Loop

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, (2,773 reviews)
"Best stay, wonderful property."
Canada
Bonnie
The price is CA $185
CA $269 total
includes taxes & fees
Nov 23 - Nov 24
Sable at Navy Pier Chicago, Curio Collection by Hilton

8. 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 $158
CA $213 total
includes taxes & fees
Dec 7 - Dec 8
Le Méridien Essex Chicago

9. 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, (1,221 reviews)
"Great location from both airports. Lovely hotel clean and convenient"
United Kingdom
Kanokkan
The price is CA $197
CA $234 total
includes taxes & fees
Dec 8 - Dec 9
Hilton Vacation Club Hotel Blake Chicago

10. 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, (2,803 reviews)
"Wonderful stay!"
United States
Dejai
The price is CA $162
CA $193 total
includes taxes & fees
Nov 22 - Nov 23
Crowne Plaza Chicago West Loop by IHG

11. Best Western River North Hotel

Best Western River North Hotel
2.5 star property
River North, 12.6 km from Sleepy Hollow
7.8 out of 10, Good, (1,191 reviews)
"Good location, friendly staff!"
United States
Alexis
The price is CA $113
CA $134 total
includes taxes & fees
Dec 7 - Dec 8
Best Western River North Hotel

12. 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 $143
CA $170 total
includes taxes & fees
Nov 23 - Nov 24
ACME Hotel Chicago, Outset Collection by Hilton

13. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
10.9 km from Sleepy Hollow
9.2 out of 10, Wonderful, (401 reviews)
"It was a fantastic stay!"
United States
Elzbieta
The price is CA $146
CA $171 total
includes taxes & fees
Nov 11 - Nov 12
LIVN - West Loop Chicago

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, (1,715 reviews)
"It was a nice quiet space and very clean. The rooms is nice and I would revisit again."
United States
Tyrell
The price is CA $150
CA $179 total
includes taxes & fees
Nov 23 - Nov 24
Cambria Hotel Chicago Loop - Theatre District

15. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
River North, 12.7 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,593 reviews)
"Great hotel"
United States
Tracy
The price is CA $140
CA $167 total
includes taxes & fees
Dec 8 - Dec 9
Hampton Inn & Suites Chicago Downtown

16. 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, (2,582 reviews)
"Great location and beautiful hotel!"
United States
Jodi
The price is CA $137
CA $163 total
includes taxes & fees
Dec 8 - Dec 9
DoubleTree by Hilton Chicago - Magnificent Mile

17. The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.5 km from Sleepy Hollow
8.4 out of 10, Very good, (3,961 reviews)
"Friendly staff and great location"
United States
Alexis
The price is CA $114
CA $136 total
includes taxes & fees
Dec 7 - Dec 8
The Whitehall Hotel, BW Premier Collection

18. La Quinta Inn & Suites by Wyndham Chicago Downtown

La Quinta Inn & Suites by Wyndham Chicago Downtown
3.0 star property
The Loop, 11.6 km from Sleepy Hollow
8.4 out of 10, Very good, (2,948 reviews)
"Overall a great stay. It was clean and we had a comfortable place to stay."
United States
Andres
The price is CA $161
CA $217 total
includes taxes & fees
Nov 23 - Nov 24
La Quinta Inn & Suites by Wyndham Chicago Downtown

19. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,370 reviews)
"Great hotel"
United States
Kristopher Joel
The price is CA $164
CA $195 total
includes taxes & fees
Nov 23 - Nov 24
citizenM Chicago Downtown

20. 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, (1,009 reviews)
"Nice environment and very reasonable prices..right downtown so great location!"
United States
Ebony
The price is CA $168
CA $200 total
includes taxes & fees
Dec 3 - Dec 4
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio 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.

Compare top hotels in Sleepy Hollow

2.5 star property
The Loop, 11.5 km from Sleepy Hollow
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
3.0 star property
West Loop, 10.8 km from Sleepy Hollow
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
3.5 star property
10.6 km from Sleepy Hollow
8.2
Very good
2,742 reviews
8.6
Excellent
3,530 reviews
8.6
Excellent
1,272 reviews
8.8
Excellent
2,196 reviews
9.0
Wonderful
1,311 reviews
The price is CA $121
CA $144 total
includes taxes & fees
Dec 7 - Dec 8
The price is CA $153
CA $223 total
includes taxes & fees
Nov 27 - Nov 28
The price is CA $143
CA $187 total
includes taxes & fees
Nov 23 - Nov 24
The price is CA $135
CA $161 total
includes taxes & fees
Dec 9 - Dec 10
The price is CA $207
CA $246 total
includes taxes & fees
Nov 25 - Nov 26
  • No Breakfast included
  • No Pool
  • No Spa
  • No 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
  • No Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • No Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet-friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, 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 $120 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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