Hotels in Sleepy Hollow

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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, (1485)
"I really liked this location - we will stay here again. "
United States
Lynnsey
The price is S$142
includes taxes & fees
22 Dec - 23 Dec
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, (2266)
"Great staff and restaurants!!"
United States
Abigale
The price is S$184
includes taxes & fees
6 Jan - 7 Jan, 2026
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, (1296)
"Great hotel!"
United States
Julie
The price is S$243
includes taxes & fees
28 Dec - 29 Dec
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, (853)
"Great place to stay"
United States
Mason
The price is S$171
includes taxes & fees
21 Dec - 22 Dec
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, (359)
"Great hotel!"
United States
Giselle
Level Chicago Fulton Market

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, (1003)
"Good place to stay in."
United States
Joan
The price is S$193
includes taxes & fees
21 Dec - 22 Dec
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Fulton Market, 11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1005)
"Awesome hotel"
United States
Eligija
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, (1004)
"We enjoyed the staying for the location "
United States
CARLOS ALBERTO
The price is S$182
includes taxes & fees
1 Jan - 2 Jan, 2026
Springhill Suites by Marriott Chicago Downtown/ River North

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2266)
"Lovely hotel! Exceptionally clean and affordable!"
United States
Robin
The price is S$282
includes taxes & fees
18 Dec - 19 Dec
Sofitel Chicago Magnificent Mile

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, (1002)
"Good service & nice clean rooms "
United States
Yessica
The price is S$181
includes taxes & fees
26 Dec - 27 Dec
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, (4114)
"Great stay"
United States
Ericka
The price is S$156
includes taxes & fees
21 Dec - 22 Dec
citizenM Chicago Downtown

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, (3437)
"Loved the location and view!"
United States
Erica
The price is S$198
includes taxes & fees
4 Jan - 5 Jan, 2026
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, (1787)
"Hotel was amazing all around! Friendly and very helpful staff. Clean rooms and a Starbucks! "
United States
Alicia
The price is S$246
includes taxes & fees
28 Dec - 29 Dec
Radisson Blu Aqua Hotel Chicago

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
8.4 out of 10, Very good, (4246)
"Excellent location Restaurant attached "
United States
Rebecca
The price is S$125
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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, (1259)
"Solid stay in a great part of town"
United States
Michael
The price is S$195
includes taxes & fees
29 Dec - 30 Dec
The Chicago Hotel Collection Ambassador Gold Coast

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop
3.5 star property
Fulton Market, 10.6 km from Sleepy Hollow
8.8 out of 10, Excellent, (1130)
"I always come back to this Hotel everything is close the area is full of things to do really love staying here !!"
United States
Sandra
The price is S$205
includes taxes & fees
21 Dec - 22 Dec
Hyatt House Chicago West Loop

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, (1004)
"Great ubicación and great breakfast "
United States
Andrea
The price is S$115
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk
4.0 star property
Streeterville, 13.2 km from Sleepy Hollow
8.4 out of 10, Very good, (1580)
"Rooms were very nice and staff was great"
United States
Nancy
The price is S$265
includes taxes & fees
21 Dec - 22 Dec
Sheraton Grand Chicago Riverwalk

The Emily Hotel

The Emily Hotel
4.0 star property
Fulton Market, 11.1 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1282)
"Very pleasant stay for my birthday! Will definitely come back and recommend to others! Top notch service and rooms were beautiful and comfortable!"
United States
Daniela
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, (2197)
"Yes, very clean room and great hospitality "
United States
leticia i Vasquez
The price is S$136
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Chicago - Magnificent 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

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.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top Sleepy Hollow Hotel Reviews

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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.