Find hotels in Sleepy Hollow, Chicago from NT$2,713

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 12 - Dec 13
Tomorrow
Dec 13 - Dec 14
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Sleepy Hollow hotels

View from room
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, (3475)
"Great place to stay "
United States
RaShawna
The price is NT$2,532
NT$2,973 total
includes taxes & fees
Jan 11 - 2026/1/12
Hilton Chicago/Magnificent Mile Suites
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
8.2 out of 10, Very Good, (2741)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is NT$2,276
NT$3,589 total
includes taxes & fees
Dec 23 - Dec 24
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Exterior
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
River North, 12 km from Sleepy Hollow
8.8 out of 10, Excellent, (3460)
"Amazing stay, beautiful view!"
United States
Joshua
The price is NT$3,288
NT$3,860 total
includes taxes & fees
Dec 14 - Dec 15
voco Chicago Downtown - Riverwalk by IHG
Lobby
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, (2956)
"Great location and great staff!!"
United States
lynne
The price is NT$2,532
NT$2,973 total
includes taxes & fees
Jan 4 - 2026/1/5
Aloft Chicago Mag Mile
2 restaurants, breakfast, lunch, dinner served; American cuisine
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, (3426)
"Great Hotel!"
United States
Siranush
The price is NT$4,076
NT$4,785 total
includes taxes & fees
Jan 4 - 2026/1/5
LondonHouse Chicago, Curio Collection by Hilton
Reception hall
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
River North, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3148)
"Great location "
United States
Christian
The price is NT$2,701
NT$3,171 total
includes taxes & fees
Jan 11 - 2026/1/12
Eurostars Magnificent Mile
Indoor pool
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2620)
"Great hotel, best location, nice and very helpful staff "
United States
Carlos
The price is NT$4,596
NT$6,395 total
includes taxes & fees
Jan 10 - 2026/1/11
InterContinental Chicago Magnificent Mile by IHG
Lobby
Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
River North, 12.7 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1328)
"It was a great stay!"
United States
Chase
The price is NT$2,845
NT$3,339 total
includes taxes & fees
Jan 5 - 2026/1/6
Hampton Inn & Suites Chicago Downtown
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Theatre District, 12.2 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2116)
"Great hotel. Very affordable for such a perfect location."
United States
Nicholas
Silversmith Hotel Chicago Downtown
2 bars/lounges
Hyatt Regency Chicago

Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3390)
"I always love staying at this place when I visit"
Canada
William
The price is NT$4,242
NT$5,896 total
includes taxes & fees
Dec 29 - Dec 30
Hyatt Regency Chicago
2 bars/lounges, rooftop bar
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 location and restaurant "
United Kingdom
Asvin
The price is NT$4,332
NT$6,003 total
includes taxes & fees
Jan 4 - 2026/1/5
theWit Chicago, a Hilton Hotel
Lobby
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (5384)
"excellent hotel "
United States
Myounghee
The price is NT$3,001
NT$3,523 total
includes taxes & fees
Jan 6 - 2026/1/7
Embassy Suites by Hilton Chicago Downtown River North
Indoor wedding
Swissotel - Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3009)
"Very beautiful place to stay"
United States
FaithBrenda
The price is NT$3,555
NT$5,089 total
includes taxes & fees
Jan 5 - 2026/1/6
Swissotel - Chicago
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, (2183)
"The staff was amazing , can’t wait to return "
United States
Jasmin
The price is NT$2,788
NT$3,273 total
includes taxes & fees
Dec 21 - Dec 22
DoubleTree by Hilton Chicago - Magnificent Mile
Rooftop bar, alfresco dining, open daily
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, (1920)
"Good value, great cleaning staff "
United Kingdom
farzana
The price is NT$3,118
NT$4,393 total
includes taxes & fees
Jan 5 - 2026/1/6
The Godfrey Hotel Chicago
Indoor pool
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, (4235)
"Clean room, very friendly staff and great location "
United States
Marcia
The price is NT$2,704
NT$3,174 total
includes taxes & fees
Dec 25 - Dec 26
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Traditional Room, 2 Queen Beds | Property entrance
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, (1157)
"Clean room, friendly staff, perfect location"
United States
Matt
The price is NT$3,275
NT$3,845 total
includes taxes & fees
Dec 21 - Dec 22
Aloft Chicago Downtown River North
Lobby sitting area
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago
4.0 star property
The Loop, 12.7 km from Sleepy Hollow
8.8 out of 10, Excellent, (1976)
"A good place for stay "
United States
Julio
The price is NT$2,311
NT$2,713 total
includes taxes & fees
Dec 28 - Dec 29
Club Quarters Hotel Wacker at Michigan, Chicago
Breakfast, lunch, dinner served; American cuisine
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North
4.5 star property
River North, 12.8 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2312)
"Wonderful customer service, great location! "
United States
Michelle
The price is NT$3,470
NT$5,074 total
includes taxes & fees
Jan 4 - 2026/1/5
The Royal Sonesta Chicago River North
Property amenity
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, (1455)
"Clean, modern, friendly/helpful staff, the perfect spot for staying for a show at The Chicago Theatre. Parking was close and easy too. "
United States
Megan
The price is NT$2,822
NT$3,313 total
includes taxes & fees
Jan 4 - 2026/1/5
Cambria Hotel Chicago Loop - Theatre District
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.
View all properties

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most.
Downtown Chicago showing 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

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

The Loop - Downtown which includes a river or creek

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

River North showing railway items, street scenes and a city

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

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 the city at Washington Station or Monroe Station (Blue Line).

Top Sleepy Hollow Hotel Reviews

River Hotel

River Hotel

10/10 Excellent
"The staff was amazing and our room was just as good. Can’t wait to come back!"
Jonathan 2-night trip
Posted 7 hours ago
River Hotel

Explore a world of travel with Expedia

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.
Where can I learn more about changing or cancelling my trip to Sleepy Hollow?
For more information about picking new dates or cancelling your trip to Sleepy Hollow, click here.
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.