Hotels in Sleepy Hollow, Chicago

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Check prices for these dates

Tonight
15 Dec - 16 Dec
Tomorrow
16 Dec - 17 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

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Our top choices for Sleepy Hollow hotels

Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

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 RM282
RM451 total
includes taxes & fees
4 Jan - 5 Jan 2026
Claridge House Chicago, Tapestry Collection by Hilton
Terrace/patio
Sable at Navy Pier Chicago, Curio 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 RM379
RM585 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Restaurant
Thompson Chicago, by Hyatt

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 RM553
RM769 total
includes taxes & fees
5 Jan - 6 Jan 2026
Thompson Chicago, by Hyatt
Exterior
Moxy Chicago Downtown

Moxy Chicago Downtown

Moxy Chicago Downtown
3.0 star property
River North, 12.5 km from Sleepy Hollow
9.4 out of 10, Exceptional, (854)
"Great place to stay"
United States
Mason
The price is RM460
RM541 total
includes taxes & fees
28 Dec - 29 Dec
Moxy Chicago Downtown
Executive lounge
Level Chicago Fulton Market

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
Terrace/patio
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

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, (1004)
"Good place to stay in."
United States
Joan
The price is RM521
RM612 total
includes taxes & fees
2 Jan - 3 Jan 2026
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3 bars/lounges, piano bar
The Hoxton Chicago

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Fulton Market, 11 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1007)
"Awesome hotel"
United States
Eligija
The Hoxton Chicago
Exterior
Springhill Suites by Marriott Chicago Downtown/ River North

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, (1007)
"We enjoyed the staying for the location "
United States
CARLOS ALBERTO
The price is RM492
RM577 total
includes taxes & fees
1 Jan - 2 Jan 2026
Springhill Suites by Marriott Chicago Downtown/ River North
Bathroom
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
13.4 km from Sleepy Hollow
9.4 out of 10, Exceptional, (2269)
"Lovely hotel! Exceptionally clean and affordable!"
United States
Robin
The price is RM659
RM894 total
includes taxes & fees
25 Dec - 26 Dec
Sofitel Chicago Magnificent Mile
Exterior
Hampton Inn Chicago West Loop Fulton Market Area

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, (1003)
"Good service & nice clean rooms "
United States
Yessica
The price is RM488
RM573 total
includes taxes & fees
28 Dec - 29 Dec
Hampton Inn Chicago West Loop Fulton Market Area
Property amenity
citizenM 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, (4118)
"Great stay"
United States
Ericka
The price is RM422
RM495 total
includes taxes & fees
21 Dec - 22 Dec
citizenM Chicago Downtown
Lobby
LondonHouse Chicago, Curio Collection by Hilton

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, (3441)
"Loved the location and view!"
United States
Erica
The price is RM534
RM626 total
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers
Radisson Blu Aqua Hotel Chicago

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)
"Friendly staff and good location to all of the city"
United States
Mark
The price is RM573
RM779 total
includes taxes & fees
29 Dec - 30 Dec
Radisson Blu Aqua Hotel Chicago
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

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, (4249)
"Excellent location Restaurant attached "
United States
Rebecca
The price is RM357
RM419 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Terrace/patio
The Chicago Hotel Collection Ambassador Gold Coast

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 RM528
RM619 total
includes taxes & fees
28 Dec - 29 Dec
The Chicago Hotel Collection Ambassador Gold Coast
City view from property
Hyatt House Chicago West Loop

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 RM553
RM649 total
includes taxes & fees
28 Dec - 29 Dec
Hyatt House Chicago West Loop
Pillow-top beds, desk, blackout curtains, iron/ironing board
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

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, (1005)
"The room was huge, great stay, clean, convenient, comfortable and great staff. "
United States
Madeline
The price is RM311
RM366 total
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Meeting facility
Sheraton Grand Chicago Riverwalk

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 RM611
RM840 total
includes taxes & fees
21 Dec - 22 Dec
Sheraton Grand Chicago Riverwalk
Exterior
The Emily Hotel

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
Terrace/patio
DoubleTree by Hilton Chicago - 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, (2200)
"Yes, very clean room and great hospitality "
United States
leticia i Vasquez
The price is RM366
RM429 total
includes taxes & fees
25 Dec - 26 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.
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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
Downtown Chicago which includes a city

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 - River North

Magnificent Mile

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

The Loop - Downtown featuring a river or creek

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.

Chicago showing rides

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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"👍"
Cesar 2-night trip
Posted 23 hours ago
Hilton Chicago/Magnificent Mile Suites

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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.