Sleepy Hollow hotels in Chicago

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Our top choices for Sleepy Hollow hotels

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, (1,519 reviews)
"Great location, friendly staff and nice room"
United States
Srinivasa
The price is HK$441
HK$747 total
includes taxes & fees
22 Feb - 23 Feb
Claridge House Chicago, Tapestry Collection by Hilton

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, (2,341 reviews)
"Great stay"
United States
Blake
The price is HK$889
HK$1,310 total
includes taxes & fees
9 Feb - 10 Feb
Sable at Navy Pier Chicago, Curio Collection by Hilton

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Gold Coast, 13.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,314 reviews)
"great stay"
United States
Loan
The price is HK$1,054
HK$1,467 total
includes taxes & fees
1 Mar - 2 Mar
Thompson Chicago, by Hyatt

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (879 reviews)
"Clean, friendly staff, and excellent location "
United States
Paulina
The price is HK$796
HK$935 total
includes taxes & fees
8 Feb - 9 Feb
Moxy Chicago Downtown

Level Chicago Fulton Market

Level Chicago Fulton Market
4.0 star property
West Loop, 11.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (393 reviews)
"The hotel in it’s entirety was better than advertised "
United States
Eric
Level Chicago Fulton Market

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,324 reviews)
"The rooms are beautiful and the staff is wonderful."
United States
Melissa
The price is HK$1,320
HK$1,778 total
includes taxes & fees
31 Jan - 1 Feb
Sofitel Chicago Magnificent Mile

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,001 reviews)
"Amazing, I loved my stay"
United States
Valerie
The Hoxton Chicago

Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1,033 reviews)
" Clean rooms Hot shower great after a freezing cold day Staff all polite and helpful Great location "
United Kingdom
John
The price is HK$829
HK$973 total
includes taxes & fees
15 Feb - 16 Feb
Springhill Suites by Marriott Chicago Downtown/ River North

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, (1,001 reviews)
"Nice hotel and staff. "
United States
Wendy
The price is HK$988
HK$1,160 total
includes taxes & fees
6 Feb - 7 Feb
Hampton Inn Chicago West Loop Fulton Market Area

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,216 reviews)
"Very nice Hotel, great atmosphere friendly staff. I had a great stay!"
United States
Lucie Saint Jean
The price is HK$734
HK$861 total
includes taxes & fees
3 Feb - 4 Feb
citizenM Chicago Downtown

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
10.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1,171 reviews)
"Staff is wonderful, nice clean rooms, centrally located, loved staying here. "
United States
Cassandra
The price is HK$1,123
HK$1,319 total
includes taxes & fees
5 Feb - 6 Feb
Hyatt House Chicago West Loop

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,574 reviews)
"Staff was kind and it was at a great location! "
Canada
Kiran
The price is HK$1,209
HK$1,419 total
includes taxes & fees
15 Feb - 16 Feb
LondonHouse Chicago, Curio Collection by Hilton

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, (1,280 reviews)
"Great hotel at an affordable price "
United States
Dhruv
The price is HK$780
HK$915 total
includes taxes & fees
1 Feb - 2 Feb
The Chicago Hotel Collection Ambassador Gold Coast

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
River North, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (4,345 reviews)
"All things about this hotel was good from the location to the staff"
United States
Cisco
The price is HK$665
HK$781 total
includes taxes & fees
5 Feb - 6 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago
4.5 star property
12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (1,840 reviews)
"Beautiful hotel nice friendly staff. I loved the view. "
United States
Nicole
The price is HK$1,229
HK$1,645 total
includes taxes & fees
15 Feb - 16 Feb
Radisson Blu Aqua Hotel Chicago

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, (1,946 reviews)
"Very convenient place to stay friendly and helpful staff."
United States
Rick
The price is HK$633
HK$743 total
includes taxes & fees
5 Feb - 6 Feb
ACME Hotel Chicago, Outset Collection by Hilton

The Emily Hotel

The Emily Hotel
4.0 star property
11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,300 reviews)
"Hotel was very stylish…hotel bar and food was great too. Staff was courteous and rooms were clean, we will stay here again. "
United States
Mary
The Emily Hotel

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, (2,270 reviews)
"amazing stay"
United States
Anani
The price is HK$665
HK$781 total
includes taxes & fees
5 Feb - 6 Feb
DoubleTree by Hilton Chicago - Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very good, (2,804 reviews)
"Great hotel staff and location. "
United States
Jacqueline
The price is HK$866
HK$1,245 total
includes taxes & fees
15 Feb - 16 Feb
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,063 reviews)
"Great location and friendly staff. "
United States
Pablo
The price is HK$663
HK$778 total
includes taxes & fees
5 Feb - 6 Feb
Aloft Chicago Mag Mile
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.

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas 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

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

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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.

O'Hare

Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago.

Top Sleepy Hollow Hotel Reviews

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?
Hawthorne Works Museum, Balzekas Museum of Lithuanian Culture and Wintrust Sports Complex are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.

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