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Check prices for these dates

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16 Jan - 17 Jan
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17 Jan - 18 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

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Our top choices for Sleepy Hollow hotels

Exterior

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, (1,517 reviews)
"Clean room, staff was very nice and it was in a very nice location! "
United States
Mary
The price is 1.486.413 ₫
2.515.953 ₫ total
includes taxes & fees
3 Feb - 4 Feb
Claridge House Chicago, Tapestry Collection by Hilton
Meeting facility

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, (1,309 reviews)
"Love this hotel, right in the middle of a great area re: restaurants, bars, night scene, etc. "
United States
Yoshio
The price is 3.546.585 ₫
4.938.331 ₫ total
includes taxes & fees
30 Jan - 31 Jan
Thompson Chicago, by Hyatt
Terrace/patio

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, (2,316 reviews)
"Great stay!"
United States
Angela
The price is 2.769.596 ₫
4.145.961 ₫ total
includes taxes & fees
27 Jan - 28 Jan
Sable at Navy Pier Chicago, Curio Collection by Hilton
Serves breakfast, lunch and dinner

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (868 reviews)
"Great hotel, lots of fun and great location! "
United States
Amber
The price is 2.837.268 ₫
3.330.668 ₫ total
includes taxes & fees
25 Jan - 26 Jan
Moxy Chicago Downtown
Smart TV

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, (382 reviews)
"The experience of the hotel was amazing"
United States
Lachelle
Level Chicago Fulton Market
2 restaurants, breakfast, lunch, dinner served; Mediterranean cuisine

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,000 reviews)
"The Hoxton was such s beautiful place to stay, I loved the convenience of a speakeasy and a restaurant and bar in one spot, not only that it is conveniently located in a area where so many bars and restaurants are in walking distance"
United States
Shavon
The Hoxton Chicago
Terrace/patio

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, (1,002 reviews)
"Room was clean staff wasexcellent breakfast was great"
United States
Jerry
The price is 3.425.213 ₫
4.020.857 ₫ total
includes taxes & fees
23 Jan - 24 Jan
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Presidential Suite, 1 King Bed | Bathroom | Separate bathtub and shower, designer toiletries, hair dryer, bathrobes

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2,327 reviews)
"Great hotel !"
United States
Dr. Mark
The price is 4.220.436 ₫
5.725.764 ₫ total
includes taxes & fees
19 Jan - 20 Jan
Sofitel Chicago Magnificent Mile
Exterior

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, (1,016 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 2.791.294 ₫
3.276.700 ₫ total
includes taxes & fees
23 Jan - 24 Jan
Springhill Suites by Marriott Chicago Downtown/ River North
City view from property

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, (1,157 reviews)
"The room was comfortable, the breakfast was nice and the staff (in person) were responsive. It's also in a good location. "
Canada
Carol
The price is 3.783.024 ₫
4.440.891 ₫ total
includes taxes & fees
22 Jan - 23 Jan
Hyatt House Chicago West Loop
Exterior

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, (1,005 reviews)
"Nice hotel and staff. "
United States
Wendy
The price is 3.327.222 ₫
3.905.825 ₫ total
includes taxes & fees
23 Jan - 24 Jan
Hampton Inn Chicago West Loop Fulton Market Area
Cocktail bar

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, (1,943 reviews)
"Love the location, room, staff, and bar."
United States
Jason
The price is 1.917.258 ₫
2.250.670 ₫ total
includes taxes & fees
22 Jan - 23 Jan
ACME Hotel Chicago, Outset Collection by Hilton
2 restaurants, breakfast, lunch, dinner served; American cuisine

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, (3,535 reviews)
"Clean accommodations and friendly staff."
United States
usha
The price is 3.640.635 ₫
4.273.740 ₫ total
includes taxes & fees
25 Jan - 26 Jan
LondonHouse Chicago, Curio Collection by Hilton
Lobby

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, (1,001 reviews)
"Great location, friendly staff, clean rooms"
United States
Jared
The price is 2.338.119 ₫
2.744.717 ₫ total
includes taxes & fees
22 Jan - 23 Jan
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Lunch and dinner served

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, (1,816 reviews)
"Great hotel"
United States
Yavuz
The price is 4.046.658 ₫
5.433.576 ₫ total
includes taxes & fees
1 Feb - 2 Feb
Radisson Blu Aqua Hotel Chicago
Exterior detail

The Emily Hotel

The Emily Hotel
4.0 star property
11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,294 reviews)
"The room was spotless, the people were accommodating and very nice, and it was a great quiet stay! "
United States
Stephanie
The price is 8.730.481 ₫
10.248.711 ₫ total
includes taxes & fees
20 Jan - 21 Jan
The Emily Hotel
Property amenity

citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Theatre District, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (4,196 reviews)
"Stay was great and in a great location!! "
United States
Ashley
The price is 2.546.241 ₫
2.989.032 ₫ total
includes taxes & fees
1 Feb - 2 Feb
citizenM Chicago Downtown
Indoor pool

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, (4,319 reviews)
"Amazing staff and perfect location "
United States
Brandi
The price is 2.068.053 ₫
2.427.688 ₫ total
includes taxes & fees
27 Jan - 28 Jan
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Lobby

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, (1,267 reviews)
"Solid stay in a great part of town"
United States
Michael
The price is 2.887.842 ₫
3.390.258 ₫ total
includes taxes & fees
21 Jan - 22 Jan
The Chicago Hotel Collection Ambassador Gold Coast
Exterior

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
River North, 11.9 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,111 reviews)
"Excellent hotel plus very good location"
Canada
Tomas Colocol
The price is 2.880.615 ₫
3.381.553 ₫ total
includes taxes & fees
18 Jan - 19 Jan
Holiday Inn Chicago Dwtn - The Mart by IHG
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.
Downtown Chicago featuring a city

Downtown Chicago

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile - River North

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

The Loop - Downtown featuring a river or creek

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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.

Rosemont

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.