Sleepy Hollow Hotels near Chicago

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Tonight
Jan 2 - Jan 3
Tomorrow
Jan 3 - Jan 4
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

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Our top choices for Sleepy Hollow hotels

In-room safe, desk, laptop workspace, blackout drapes
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

Aloft Chicago Downtown River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.4 out of 10, Exceptional, (1176)
"Great stay!"
United States
Tea
The price is P6,256
P7,343 total
includes taxes & fees
Jan 11 - Jan 12
Aloft Chicago Downtown River North
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, (3492)
"Great hotel! "
United States
Kianna
The price is P8,157
P9,576 total
includes taxes & fees
Feb 1 - Feb 2
LondonHouse Chicago, Curio Collection by Hilton
Exterior
L7 Chicago by LOTTE

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (3473)
"Amazing place to stay and super accommodating "
United States
Carson
The price is P8,298
P9,741 total
includes taxes & fees
Jan 16 - Jan 17
L7 Chicago by LOTTE
Lobby
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel
4.5 star property
Theatre District, 12.4 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1001)
"Great views and super comfortable bed. "
United States
Keely
The price is P8,642
P11,873 total
includes taxes & fees
Jan 11 - Jan 12
theWit Chicago, a Hilton Hotel
Bar (on property)
Omni Chicago Hotel

Omni Chicago Hotel

Omni Chicago Hotel
4.5 star property
Magnificent Mile, 13.3 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1658)
"Great place to stay "
United States
Juliet
The price is P9,374
P12,732 total
includes taxes & fees
Jan 4 - Jan 5
Omni Chicago Hotel
American cuisine, alfresco dining
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago
4.5 star property
River North, 12.8 km from Sleepy Hollow
8.6 out of 10, Excellent, (1968)
"The room was nice, the area was perfect for walking distance for food and activities. "
United States
Alexis
The price is P5,133
P7,407 total
includes taxes & fees
Feb 2 - Feb 3
The Godfrey Hotel Chicago
Premium bedding, down comforters, pillowtop beds, in-room safe
The Wade

The Wade

The Wade
4.5 star property
Streeterville, 13.8 km from Sleepy Hollow
8.4 out of 10, Very Good, (1563)
"Great staff and great location. "
United States
Joe
The price is P5,455
P6,403 total
includes taxes & fees
Jan 8 - Jan 9
The Wade
Exterior
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, (2290)
"Great hotel "
United States
Shantasha
The price is P9,458
P12,832 total
includes taxes & fees
Jan 6 - Jan 7
Sofitel Chicago Magnificent Mile
Exterior
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1055)
"Clean room, clean hotel, wonderful restaurant/bar. AMAZING location! "
United States
Rebecca
The price is P5,770
P8,501 total
includes taxes & fees
Jan 11 - Jan 12
Hyatt Centric Chicago Magnificent Mile
Reception
Swissotel - Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3082)
"Amazing staff and location beautiful hotel "
United States
RANDIE
The price is P6,711
P9,606 total
includes taxes & fees
Jan 5 - Jan 6
Swissotel - Chicago
Restaurant
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.4 out of 10, Very Good, (1809)
"Very clean and comfortable hotel!"
United States
HYUNJI
Hotel Saint Clair- Magnificent Mile
Front of property
Ivy Boutique Hotel

Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Streeterville, 13.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (1061)
"My favorite hotel for a staycation"
United States
SABRINA L
Ivy Boutique Hotel
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, (863)
"Great hotel, lots of fun and great location! "
United States
Amber
The price is P6,005
P7,050 total
includes taxes & fees
Jan 11 - Jan 12
Moxy Chicago Downtown
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Streeterville, 13.8 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3651)
"Great place to stay "
United States
RaShawna
The price is P5,262
P6,177 total
includes taxes & fees
Jan 8 - Jan 9
Hilton Chicago/Magnificent Mile Suites
Lobby sitting area
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.2 out of 10, Very Good, (2492)
"The room was amazing and the customer service was great!"
United States
Chelsi
Hotel Felix River North/Magnificent Mile
Exterior
AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown

AC Hotels by Marriott Chicago Downtown
4.0 star property
River North, 13.1 km from Sleepy Hollow
8.8 out of 10, Excellent, (1006)
"Very nice cozy hotel "
United States
CARLA
The price is P5,935
P6,967 total
includes taxes & fees
Feb 1 - Feb 2
AC Hotels by Marriott Chicago Downtown
Snack bar
Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
8.8 out of 10, Excellent, (1481)
"Great room and friendly staff. Great place to stay for the price. I Would definitely recommend this hotel to a friend. "
United States
Timothy
The price is P5,273
P6,190 total
includes taxes & fees
Jan 25 - Jan 26
Cambria Hotel Chicago Loop - Theatre District
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
8.6 out of 10, Excellent, (4306)
"Amazing staff and perfect location "
United States
Brandi
The price is P4,586
P5,384 total
includes taxes & fees
Jan 11 - Jan 12
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Cocktail bar
Aloft Chicago Mag 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, (3004)
"Great place to stay"
United States
Elisha
The price is P4,946
P5,806 total
includes taxes & fees
Jan 6 - Jan 7
Aloft Chicago Mag Mile
Exterior
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
4.5 star property
Theatre District, 12.5 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1412)
"Staff was wonderful."
United States
Jamie
The price is P7,556
P10,528 total
includes taxes & fees
Jan 11 - Jan 12
Sports Illustrated Resorts Chicago
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 and neighborhoods 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 showing 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 which includes 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 the city at Washington Station or Monroe Station (Blue Line).

Top Sleepy Hollow Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Staff was amazing room eh was ok. The service was great though and they gave us fans and extra blankets no problem!"
Christopher 3-night trip
Posted 6 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Frequently asked questions

What's it like in Sleepy Hollow?
Sleepy Hollow is a neighborhood that travelers 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to get the best deals available in Sleepy Hollow.
What can I see and do in this Chicago neighborhood?
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.