Chicago Hotel Guide. Hotels in Sleepy Hollow, Chicago, United States of America

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
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Sleepy Hollow hotels

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, (3482)
"Great place to stay "
United States
RaShawna
The price is €81
includes taxes & fees
8 Jan - 9 Jan 2026
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, (2742)
"Clean room and friendly staff, overall good stay "
United States
eesaa saalik
The price is €118
includes taxes & fees
15 Dec - 16 Dec
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Bar (on property)
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, (3462)
"Amazing stay, beautiful view!"
United States
Joshua
The price is €115
includes taxes & fees
29 Dec - 30 Dec
voco Chicago Downtown - Riverwalk by IHG
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, (2958)
"Great location and great staff!!"
United States
lynne
The price is €79
includes taxes & fees
14 Jan - 15 Jan 2026
Aloft Chicago Mag Mile
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, (3433)
"Great Hotel!"
United States
Siranush
The price is €130
includes taxes & fees
4 Jan - 5 Jan 2026
LondonHouse Chicago, Curio Collection by Hilton
Reception
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, (3151)
"Amazing stay very clean and beautiful views "
United States
Deigo
The price is €94
includes taxes & fees
12 Jan - 13 Jan 2026
Eurostars Magnificent Mile
Exterior
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, (2621)
"Great hotel, best location, nice and very helpful staff "
United States
Carlos
The price is €170
includes taxes & fees
11 Jan - 12 Jan 2026
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, (1329)
"The front desk was amazing!! And housekeeping was so accommodating!! Great location!!! Great breakfast!"
United States
julie
The price is €91
includes taxes & fees
4 Jan - 5 Jan 2026
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, (2121)
"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, (3393)
"I always love staying at this place when I visit"
Canada
William
The price is €161
includes taxes & fees
28 Dec - 29 Dec
Hyatt Regency Chicago
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, (1002)
"Great location and restaurant "
United Kingdom
Asvin
The price is €164
includes taxes & fees
4 Jan - 5 Jan 2026
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, (5387)
"excellent hotel "
United States
Myounghee
The price is €96
includes taxes & fees
6 Jan - 7 Jan 2026
Embassy Suites by Hilton Chicago Downtown River North
Reception
Swissotel - Chicago

Swissotel - Chicago

Swissotel - Chicago
4.5 star property
13 km from Sleepy Hollow
9.0 out of 10, Wonderful, (3012)
"Very beautiful place to stay"
United States
FaithBrenda
The price is €139
includes taxes & fees
1 Jan - 2 Jan 2026
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, (2189)
"Yes, very clean room and great hospitality "
United States
leticia i Vasquez
The price is €89
includes taxes & fees
21 Dec - 22 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
American cuisine, al fresco 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, (1922)
"Good value, great cleaning staff "
United Kingdom
farzana
The price is €120
includes taxes & fees
4 Jan - 5 Jan 2026
The Godfrey 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, (4239)
"Clean room, very friendly staff and great location "
United States
Marcia
The price is €87
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Room, 2 Queen Beds, Corner (View)
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, (1159)
"Clean room, friendly staff, perfect location"
United States
Matt
The price is €105
includes taxes & fees
21 Dec - 22 Dec
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, (1981)
"A good place for stay "
United States
Julio
The price is €83
includes taxes & fees
15 Dec - 16 Dec
Club Quarters Hotel Wacker at Michigan, Chicago
Terrace/patio
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, (2314)
"Wonderful customer service, great location! "
United States
Michelle
The price is €138
includes taxes & fees
4 Jan - 5 Jan 2026
The Royal Sonesta Chicago River North
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, (1457)
"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 €87
includes taxes & fees
4 Jan - 5 Jan 2026
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 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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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 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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Great place always. "
Robert 1-night trip
Posted 2 days ago
Embassy Suites by Hilton Chicago Downtown River North

Explore a world of travel with Expedia

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.