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Sleepy Hollow Hotels, Chicago

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Check prices for these dates

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

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Our top choices for Sleepy Hollow hotels

Terrace/patio

1. 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, (2,641 reviews)
"Nice Stay"
United States
Morgan
The price is NZ$433
includes taxes & fees
30 Aug - 31 Aug
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior

2. 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, (2,440 reviews)
"Great location"
United States
Navin
The price is NZ$341
includes taxes & fees
20 Aug - 21 Aug
Crowne Plaza Chicago West Loop by IHG
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

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, (1,110 reviews)
"Great Stay. Perfect area for activities, clean room, and wonderful staff member who showed excellent hospitality and convenience."
United States
Erick
The price is NZ$327
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn & Suites Chicago - Downtown by IHG
Restaurant

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, (2,748 reviews)
"Good stay!"
United States
Adit
The price is NZ$326
includes taxes & fees
30 Aug - 31 Aug
Best Western Grant Park Hotel
City view from property

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, (1,312 reviews)
"Very nice hotel"
United States
Hadi
The price is NZ$473
includes taxes & fees
16 Aug - 17 Aug
Hyatt House Chicago/West Loop-Fulton Market
Pool

6. 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, (2,103 reviews)
"helpful staff, great location, comfortable rooms and great views"
United States
Jordan Leigh
The price is NZ$348
includes taxes & fees
10 Aug - 11 Aug
Hilton Garden Inn Chicago Downtown South Loop
Exterior

7. Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,291 reviews)
"Very helpful front desk staff and friendly cleaners. Very pleasant stay"
United States
Aleace
The price is NZ$343
includes taxes & fees
30 Aug - 31 Aug
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Lobby

8. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
2.0 star property
The Loop, 11.8 km from Sleepy Hollow
7.6 out of 10, Good, (2,695 reviews)
"Great location, clean rooms, would stay here again!"
United States
Adam
The price is NZ$269
includes taxes & fees
30 Aug - 31 Aug
Travelodge by Wyndham Downtown Chicago
Suite, 1 Bedroom, Corner | Private kitchen

9. 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, (2,395 reviews)
"Great stay"
United Kingdom
jayne
The price is NZ$399
includes taxes & fees
10 Aug - 11 Aug
Homewood Suites by Hilton Chicago Downtown South Loop
Exterior

10. 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
8.6 out of 10, Excellent, (2,841 reviews)
"Location is very good and staff is nice!"
United States
Diana
The price is NZ$385
includes taxes & fees
30 Aug - 31 Aug
La Quinta Inn & Suites by Wyndham Chicago Downtown
Lobby

11. 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, (10,356 reviews)
"Great place to stay"
United States
ERIC
The price is NZ$310
includes taxes & fees
30 Aug - 31 Aug
Congress Plaza Hotel
Lobby

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, (1,002 reviews)
"Room was quiet and clean"
United States
Robert
The price is NZ$356
includes taxes & fees
30 Aug - 31 Aug
Le Méridien Essex Chicago
Lobby

13. The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Gold Coast, 13.9 km from Sleepy Hollow
8.0 out of 10, Very good, (1,862 reviews)
"Great stay"
United States
Judy
The price is NZ$329
includes taxes & fees
10 Aug - 11 Aug
The Chicago Hotel Collection Ambassador Gold Coast
Exterior

14. Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
River North, 11.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,484 reviews)
"Great stay"
United States
James
The price is NZ$420
includes taxes & fees
30 Aug - 31 Aug
Holiday Inn Chicago Dwtn - The Mart by IHG
Exterior

15. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,000 reviews)
"Great location staff very friendly and helpful very clean would stay again"
United States
Michele
The price is NZ$474
includes taxes & fees
30 Aug - 31 Aug
Hampton Inn Chicago West Loop Fulton Market Area
Restaurant

16. 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, (1,405 reviews)
"Very nice would stay again"
United States
Dawn
The price is NZ$434
includes taxes & fees
30 Aug - 31 Aug
Hilton Garden Inn Chicago Central Loop
Exterior

17. 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, (1,000 reviews)
"Excellent hotel! Very clean staff very nice and respectful. Breakfast was very tasty."
United States
Naidy
The price is NZ$385
includes taxes & fees
30 Aug - 31 Aug
Hampton Inn Majestic Chicago Theatre District
Exterior

18. 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, (1,488 reviews)
"Enjoyed my stay!"
United States
Kimberly
The price is NZ$416
includes taxes & fees
16 Aug - 17 Aug
Hyatt Place Chicago/Downtown - The Loop
Terrace/patio

19. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,001 reviews)
"It’s a clean and well managed hotel."
United States
Jihi
The price is NZ$401
includes taxes & fees
16 Aug - 17 Aug
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Nightclub

20. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,234 reviews)
"Nice stay"
United States
Joseph
The price is NZ$304
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.
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Our guide on 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

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

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.

The Chicago Theatre with illuminated marquee and a wet street reflecting lights.
Photo by Mattyboy876
Open Photo by Mattyboy876

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top Sleepy Hollow Hotel Reviews

Recent Reviews in Sleepy Hollow

Omni Chicago Hotel

Omni Chicago Hotel

10/10 Excellent
"Great location. Staff was friendly and helpful. Our room was spacious and spotless. I will definitely return."
Michael 3-night trip
Posted 5 hours ago
Omni Chicago 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?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline − this is often within 24 to 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 can I save on a hotel booking in Sleepy Hollow with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Sleepy Hollow hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Sleepy Hollow?
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.