Search Hotels in Sleepy Hollow, 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, (1,518 reviews)
"Clean room, staff was very nice and it was in a very nice location! "
United States
Mary
The price is ₹5,144
₹8,707 total
includes taxes & fees
9 Feb - 10 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, (2,331 reviews)
"Great stay"
United States
Blake
The price is ₹9,196
₹13,891 total
includes taxes & fees
17 Feb - 18 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, (1,313 reviews)
"Love this hotel, right in the middle of a great area re: restaurants, bars, night scene, etc. "
United States
Yoshio
The price is ₹13,183
₹18,157 total
includes taxes & fees
12 Feb - 13 Feb
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, (872 reviews)
"Great hotel, lots of fun and great location! "
United States
Amber
The price is ₹9,410
₹11,046 total
includes taxes & fees
25 Jan - 26 Jan
Moxy Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,185 reviews)
"Super clean, friendly staff, amazing breakfast, unbeatable location"
United States
Ken
The price is ₹9,364
₹10,993 total
includes taxes & fees
26 Jan - 27 Jan
citizenM Chicago Downtown

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, (1,269 reviews)
"Solid stay in a great part of town"
United States
Michael
The price is ₹10,901
₹12,796 total
includes taxes & fees
21 Jan - 22 Jan
The Chicago Hotel Collection Ambassador Gold Coast

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,306 reviews)
"Great hotel !"
United States
Dr. Mark
The price is ₹14,605
₹19,815 total
includes taxes & fees
25 Jan - 26 Jan
Sofitel Chicago Magnificent Mile

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, (387 reviews)
"The experience of the hotel was amazing"
United States
Lachelle
Level Chicago Fulton Market

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, (4,342 reviews)
"All things about this hotel was good from the location to the staff"
United States
Cisco
The price is ₹7,753
₹9,102 total
includes taxes & fees
1 Feb - 2 Feb
Hilton Garden Inn Chicago Downtown/Magnificent Mile

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,007 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
9.2 out of 10, Wonderful, (1,022 reviews)
"Room was super clean, staff was friendly and helpful, and the area was a perfect spot in town!"
United States
Zachary
The price is ₹10,455
₹12,273 total
includes taxes & fees
25 Jan - 26 Jan
Springhill Suites by Marriott Chicago Downtown/ River North

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, (3,547 reviews)
"Clean accommodations and friendly staff."
United States
usha
The price is ₹12,599
₹14,790 total
includes taxes & fees
8 Feb - 9 Feb
LondonHouse Chicago, Curio Collection by Hilton

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, (1,832 reviews)
"Great hotel"
United States
Yavuz
The price is ₹14,001
₹18,799 total
includes taxes & fees
5 Feb - 6 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, (1,934 reviews)
"Love the location, room, staff, and bar."
United States
Jason
The price is ₹6,635
₹7,789 total
includes taxes & fees
27 Jan - 28 Jan
ACME Hotel Chicago, Outset Collection by Hilton

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)
"Nice hotel and staff. "
United States
Wendy
The price is ₹11,514
₹13,517 total
includes taxes & fees
30 Jan - 31 Jan
Hampton Inn Chicago West Loop Fulton Market Area

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection
3.5 star property
Streeterville, 13.5 km from Sleepy Hollow
8.2 out of 10, Very good, (3,888 reviews)
"Location, breakfast was good, room was nice. "
United States
Traci
The price is ₹6,959
₹8,170 total
includes taxes & fees
25 Jan - 26 Jan
The Whitehall Hotel, BW Premier Collection

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, (1,000 reviews)
"Room was clean staff wasexcellent breakfast was great"
United States
Jerry
The price is ₹11,854
₹13,915 total
includes taxes & fees
30 Jan - 31 Jan
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
2.5 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,005 reviews)
"The room was cozy and breakfast was very good and the staff were very kind and welcoming."
United States
Ibrahim
The price is ₹8,091
₹9,499 total
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

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, (2,258 reviews)
"Great staff, easy check in."
United States
Zachary
The price is ₹7,753
₹9,102 total
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Chicago - Magnificent Mile

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, (1,168 reviews)
"Only stayed one night but really enjoyed our stay. "
United States
Michael
The price is ₹13,085
₹15,360 total
includes taxes & fees
19 Feb - 20 Feb
Hyatt House Chicago West Loop
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

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

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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