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Sleepy Hollow Hotels, Chicago

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Check prices for these dates

This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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Our top choices for Sleepy Hollow hotels

Exterior detail

1. Carleton of Oak Park

Carleton of Oak Park
3.0 star property
9.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,147 reviews)
"Fantastic stay"
United States
Alan
The price is AU$144
includes taxes & fees
10 Sept - 11 Sept
Carleton of Oak Park
Superior Apartment, 2 Bedrooms, Kitchen | Living area

2. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
10.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (247 reviews)
"Great stay!"
United States
Tomas
The price is AU$198
includes taxes & fees
7 Sept - 8 Sept
LIVN - West Loop Chicago
Room

3. 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, (2,686 reviews)
"Nice place to stay"
United States
Ashraf
The price is AU$352
includes taxes & fees
8 Sept - 9 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
Lobby

4. 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, (10,265 reviews)
"The hotel offers an amazing, perfect location, and historic hotel experience."
United States
George
The price is AU$187
includes taxes & fees
7 Sept - 8 Sept
Congress Plaza Hotel
Exterior

5. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,135 reviews)
"Very nice place would stay again"
United States
Konner
The price is AU$322
includes taxes & fees
10 Sept - 11 Sept
Hilton Chicago
Restaurant

6. 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, (2,730 reviews)
"The location of the hotel is great close to many things."
United States
Melissa
The price is AU$237
includes taxes & fees
7 Sept - 8 Sept
Best Western Grant Park Hotel
Lobby

7. 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, (2,149 reviews)
"Loved this hotel, great location and wonderful accommodations, just perfect"
United States
Laura
The price is AU$202
includes taxes & fees
8 Sept - 9 Sept
The Chicago Hotel Collection Ambassador Gold Coast
Nightclub

8. Central Loop Hotel

Central Loop Hotel
4.0 star property
Theatre District, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (2,275 reviews)
"Great location."
United States
Yiyang
The price is AU$200
includes taxes & fees
7 Sept - 8 Sept
Central Loop Hotel
Front of property

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, (1,270 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 AU$301
includes taxes & fees
7 Sept - 8 Sept
Hilton Vacation Club Hotel Blake Chicago
Rooftop terrace

10. Hyatt Centric The Loop Chicago

Hyatt Centric The Loop Chicago
4.0 star property
Theatre District, 11.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,731 reviews)
"Great place to stay!"
United States
Tamika
The price is AU$352
includes taxes & fees
7 Sept - 8 Sept
Hyatt Centric The Loop Chicago
Pool

11. 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, (2,147 reviews)
"Great stay"
United States
Dhannetta
The price is AU$266
includes taxes & fees
10 Sept - 11 Sept
Hilton Garden Inn Chicago Downtown South Loop
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, (1,008 reviews)
"This hotel was perfect. Room was a great size, clean, very friendly staff. Perfect for our work trip!"
United States
amanda
The price is AU$289
includes taxes & fees
7 Sept - 8 Sept
Le Méridien Essex Chicago
Lobby

13. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,008 reviews)
"Clean rooms and good breakfast"
United States
Sarwat
The price is AU$231
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Suite, 1 Bedroom, Corner | Private kitchen

14. 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, (2,447 reviews)
"Clean, friendly staff, quick valet, and a decent breakfast"
United States
AMBER
The price is AU$287
includes taxes & fees
7 Sept - 8 Sept
Homewood Suites by Hilton Chicago Downtown South Loop
City view from property

15. 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, (1,334 reviews)
"A great hotel in a bustling area. We had a great stay."
United States
Joel
The price is AU$413
includes taxes & fees
7 Sept - 8 Sept
Hyatt House Chicago/West Loop-Fulton Market
Exterior

16. 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, (2,591 reviews)
"Loved our stay"
Canada
Jaclyn
The price is AU$320
includes taxes & fees
7 Sept - 8 Sept
Crowne Plaza Chicago West Loop by IHG
Restaurant

17. 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, (1,201 reviews)
"The hotel is so good."
United States
Julenny
The price is AU$284
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn & Suites Chicago - Downtown by IHG
Nightclub

18. 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, (3,646 reviews)
"Great location very central"
United Kingdom
Simon
The price is AU$220
includes taxes & fees
7 Sept - 8 Sept
Club Quarters Hotel, Central Loop, Chicago
Exterior

19. 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, (2,910 reviews)
"Location, good stay"
United States
Shilpa
The price is AU$297
includes taxes & fees
7 Sept - 8 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown
Lobby

20. 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, (2,819 reviews)
"Great place"
United States
Matthew
The price is AU$234
includes taxes & fees
8 Sept - 9 Sept
Travelodge by Wyndham Downtown Chicago
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

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

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 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

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"staff were very friendly and helpful"
Simon 4-night trip
Posted less than an hour ago
InterContinental Chicago Magnificent Mile by IHG

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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