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Sleepy Hollow Hotels, Chicago

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Check prices for these dates

Next weekend
24 July - 26 July
In two weeks
31 July - 2 Aug

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Our top choices for Sleepy Hollow hotels

Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

1. 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, (1,082 reviews)
"It was a decent stay."
United States
Terrell
The price is AU$267
includes taxes & fees
9 Aug - 10 Aug
Holiday Inn & Suites Chicago - Downtown by IHG
City view from property

2. 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, (1,300 reviews)
"Very nice hotel"
United States
Hadi
The price is AU$346
includes taxes & fees
26 July - 27 July
Hyatt House Chicago/West Loop-Fulton Market
Exterior

3. 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, (2,387 reviews)
"Great location- comfy bed!"
United States
Bethany
The price is AU$307
includes taxes & fees
10 Aug - 11 Aug
Crowne Plaza Chicago West Loop by IHG
Pool

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, (2,083 reviews)
"helpful staff, great location, comfortable rooms and great views"
United States
Jordan Leigh
The price is AU$343
includes taxes & fees
13 Aug - 14 Aug
Hilton Garden Inn Chicago Downtown South Loop
Suite, 1 Bedroom, Corner | Private kitchen

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, (2,392 reviews)
"Great stay"
United Kingdom
jayne
The price is AU$319
includes taxes & fees
10 Aug - 11 Aug
Homewood Suites by Hilton Chicago Downtown South Loop
Terrace/patio

6. 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, (2,592 reviews)
"View was beautiful, accommodations were excellent."
United States
Julie
The price is AU$445
includes taxes & fees
17 Aug - 18 Aug
Sable at Navy Pier Chicago, Curio Collection by Hilton
Restaurant

7. 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, (2,739 reviews)
"Nice place to stay at"
United States
Tammy
The price is AU$274
includes taxes & fees
9 Aug - 10 Aug
Best Western Grant Park Hotel
Nightclub

8. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (3,584 reviews)
"Clean room and great staff."
United States
Christopher
The price is AU$245
includes taxes & fees
16 Aug - 17 Aug
Club Quarters Hotel, Central Loop, Chicago
Lobby

9. 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, (2,685 reviews)
"Great location, walking distance to shops and eating."
United States
MARTINA
The price is AU$282
includes taxes & fees
17 Aug - 18 Aug
Travelodge by Wyndham Downtown Chicago
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, (2,829 reviews)
"Location is very good and staff is nice!"
United States
Diana
The price is AU$324
includes taxes & fees
9 Aug - 10 Aug
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

11. 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, (1,285 reviews)
"Everything where OK in my stay at the Hotel. Good location, near of everything. Definitely I'll book again there for my next trip."
United States
Carlos
The price is AU$312
includes taxes & fees
9 Aug - 10 Aug
Bluegreen Vacations Hotel Blake, an Ascend Collection 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, (1,001 reviews)
"Room was quiet and clean"
United States
Robert
The price is AU$323
includes taxes & fees
9 Aug - 10 Aug
Le Méridien Essex Chicago
Lobby

13. 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, (10,204 reviews)
"The hospitality of the staff was wonderful"
United States
Tammy C
The price is AU$321
includes taxes & fees
11 Aug - 12 Aug
Congress Plaza Hotel
Restaurant

14. 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, (1,393 reviews)
"Great stay"
United States
Malachi
The price is AU$350
includes taxes & fees
9 Aug - 10 Aug
Hilton Garden Inn Chicago Central Loop
Exterior

15. Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (4,603 reviews)
"Great place to stay"
United States
Chameka
The price is AU$264
includes taxes & fees
16 Aug - 17 Aug
Hilton Chicago/Magnificent Mile Suites
Lobby

16. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,297 reviews)
"Nice place to stay"
United States
Donilyn
The price is AU$315
includes taxes & fees
9 Aug - 10 Aug
Silversmith Hotel Chicago Downtown
Champagne service

17. The Buckingham Hotel

The Buckingham Hotel
3.5 star property
The Loop, 11.4 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,002 reviews)
"Nice place to stay"
United States
Dominique
The price is AU$347
includes taxes & fees
19 July - 20 July
The Buckingham Hotel
Lobby

18. 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
8.2 out of 10, Very good, (1,775 reviews)
"Great location, clean, and a super breakfast!"
United States
Tina
The price is AU$324
includes taxes & fees
17 Aug - 18 Aug
The Chicago Hotel Collection Ambassador Gold Coast
Lunch, dinner and brunch served

19. Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,869 reviews)
"Perfect stay."
United States
Mark
The price is AU$289
includes taxes & fees
10 Aug - 11 Aug
Hyatt Place Chicago/River North
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, (2,214 reviews)
"Great Place in Downtown for a couple of days stay"
United States
Sai Vineeth
The price is AU$271
includes taxes & fees
19 July - 20 July
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 historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.

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

Recent Reviews in Sleepy Hollow

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"The location is great, the cleanliness is appreciated and the staff are very helpful. The noise from AC was a bit annoying, but the overall experience was great."
Bissan 11-night trip
Posted 2 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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.

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