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Chicago Hotel Guide. Hotels in Sleepy Hollow, Chicago, United States of America

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Check prices for these dates

Next weekend
18 Sept - 20 Sept
In two weeks
25 Sept - 27 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, (1,153 reviews)
"Fantastic stay"
United States
Alan
The price is €117
includes taxes & fees
20 Sept - 21 Sept
Carleton of Oak Park
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, (2,632 reviews)
"It is a great location with nice rooms"
United States
Phillip
The price is €168
includes taxes & fees
20 Sept - 21 Sept
Crowne Plaza Chicago West Loop by IHG
Restaurant

3. 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, (2,740 reviews)
"Very good hotel"
United States
Diego
The price is €184
includes taxes & fees
29 Sept - 30 Sept
Best Western Grant Park Hotel
Lobby

4. 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, (2,230 reviews)
"Loved this hotel, great location and wonderful accommodations, just perfect"
United States
Laura
The price is €183
includes taxes & fees
13 Oct - 14 Oct
The Chicago Hotel Collection Ambassador Gold Coast
Lobby

5. 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, (10,231 reviews)
"Good place to stay location is amazing can’t get any better"
United States
Manuel
The price is €179
includes taxes & fees
27 Sept - 28 Sept
Congress Plaza Hotel
Exterior

6. Hilton Chicago

Hilton Chicago
4.0 star property
The Loop, 11.7 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,191 reviews)
"Enjoyable stay and a delicious breakfast."
United States
Lori
The price is €254
includes taxes & fees
25 Sept - 26 Sept
Hilton Chicago
Lobby lounge

7. 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, (1,006 reviews)
"Great stay right in the Loop and convenient to the L."
United States
Scott
The price is €163
includes taxes & fees
27 Sept - 28 Sept
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio 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, (2,839 reviews)
"Clean quiet room good location"
United States
Durant
The price is €155
includes taxes & fees
27 Sept - 28 Sept
Travelodge by Wyndham Downtown Chicago
Superior Apartment, 2 Bedrooms, Kitchen | Living area

9. LIVN - West Loop Chicago

LIVN - West Loop Chicago
4.0 star property
10.9 km from Sleepy Hollow
9.2 out of 10, Wonderful, (260 reviews)
"It was a very nice place to stay"
Canada
chidubem
The price is €151
includes taxes & fees
20 Sept - 21 Sept
LIVN - West Loop Chicago
Nightclub

10. 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, (3,643 reviews)
"Clean hotel and friendly staff"
United States
Jacqueline
The price is €190
includes taxes & fees
27 Sept - 28 Sept
Club Quarters Hotel, Central Loop, Chicago
Lobby

11. River Hotel

River Hotel
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (5,436 reviews)
"Excellent stay!!"
United States
steve
The price is €158
includes taxes & fees
27 Sept - 28 Sept
River Hotel
Exterior

12. 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, (1,218 reviews)
"Excellent Stay. Staff were wonderful and welcoming."
United States
Jennifer
The price is €201
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn & Suites Chicago - Downtown by IHG
Lobby

13. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,393 reviews)
"Loved our stay at this hotel"
Canada
Zamira
The price is €214
includes taxes & fees
21 Sept - 22 Sept
Silversmith Hotel Chicago Downtown
Exterior

14. The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Streeterville, 13.5 km from Sleepy Hollow
7.8 out of 10, Good, (2,160 reviews)
"The hotel was well located and beautiful."
United States
Patricia
The price is €124
includes taxes & fees
20 Sept - 21 Sept
The Chicago Hotel Collection - Magnificent Mile
Exterior

15. Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton
4.0 star property
Gold Coast, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,443 reviews)
"Nice upscale hotel in a great area."
United States
Christie
The price is €184
includes taxes & fees
20 Sept - 21 Sept
Claridge House Chicago, Tapestry Collection by Hilton
Property amenity

16. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,347 reviews)
"Had a great stay, would definitely book here again!"
United States
Isayra
The price is €198
includes taxes & fees
20 Sept - 21 Sept
citizenM Chicago Downtown
Terrace/patio

17. 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, (2,687 reviews)
"Amazing place to stay"
United States
Shanequa
The price is €327
includes taxes & fees
27 Sept - 28 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior

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
8.6 out of 10, Excellent, (2,908 reviews)
"Our stay was great."
United States
Mythli
The price is €217
includes taxes & fees
20 Sept - 21 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown
Serves breakfast, lunch and dinner

19. Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,002 reviews)
"Love the hotel, love the area, will repeat !"
United States
Justin
The price is €205
includes taxes & fees
20 Sept - 21 Sept
Moxy Chicago Downtown
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, (2,290 reviews)
"Great location."
United States
Yiyang
The price is €168
includes taxes & fees
20 Sept - 21 Sept
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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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
A cityscape with tall skyscrapers and a historic tower.

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 busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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 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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Nice location, clean spacious room, comfortable bed all of the things you would expect were there My only issue was a lack of electrical outlets next to the bed. In today world there should be an available outlet or two next to the bed"
Greg 1-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Frequently asked questions

What's it like in Sleepy Hollow?
Sleepy Hollow is a neighbourhood that travellers like for its restaurants.
If I need to cancel my hotel reservation in Sleepy Hollow, will I receive a refund?
Yes! The majority of hotel reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of your booking. Put your dates in and click on "Search", then filter by "fully refundable" to view the top deals on offer in Sleepy Hollow.
What can I see and do in this Chicago neighbourhood?
Douglas Park, Hawthorne Race Course and Hawthorne Works Museum are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Jedlica Performing Arts Center and Los Globos are also worth a stop.