Sleepy Hollow Hotels, Chicago

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
6 Nov - 7 Nov
Tomorrow
7 Nov - 8 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Filter by

Guest rating
Guest rating
Star rating

4833 Cheap Hotels in Sleepy Hollow - Specials, Reviews, & Last Minute Deals

Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4775)
"Beautiful hotel. Had a nice stay"
United States
Esther
The price is NZ$232
includes taxes & fees
19 Nov - 20 Nov
River Hotel
Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3080)
"Awesome location and excellent service, the staff was great!"
United States
Salvador
The price is NZ$225
includes taxes & fees
7 Dec - 8 Dec
Eurostars Magnificent Mile
Outdoor pool, pool cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2128)
"Very nice hotel "
United States
Patrick
The price is NZ$198
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
9.4 out of 10, Exceptional, (2214)
"Room was spotless…staff was great!"
United States
Tamika
The price is NZ$277
includes taxes & fees
25 Nov - 26 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2879)
"Clean room and loved the atmosphere"
United States
Madison
The price is NZ$189
includes taxes & fees
23 Nov - 24 Nov
Aloft Chicago Mag Mile
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2283)
"Great Hotel"
United States
Luz
The price is NZ$288
includes taxes & fees
24 Nov - 25 Nov
Hilton Chicago
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (4063)
"Clean rooms, friendly staff, great breakfast, amazing location. "
Canada
Gokce
The price is NZ$236
includes taxes & fees
11 Nov - 12 Nov
citizenM Chicago Downtown
American cuisine
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 star property
9.0 out of 10, Wonderful, (1657)
"Great hotel and amenities "
United States
Adrienne
The price is NZ$211
includes taxes & fees
23 Nov - 24 Nov
Crowne Plaza Chicago West Loop by IHG
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
9.0 out of 10, Wonderful, (3236)
"Overall it was a great place to stay."
United States
Edward
The price is NZ$210
includes taxes & fees
17 Nov - 18 Nov
Hilton Chicago/Magnificent Mile Suites
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9510)
"Great stay comfortable bed and great location!"
United States
Kimberly Noel
The price is NZ$334
includes taxes & fees
7 Nov - 8 Nov
Congress Plaza Hotel
Exterior
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
8.4 out of 10, Very good, (4130)
"Clean rooms and friendly staff"
United States
Jeffrey
The price is NZ$195
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2572)
"Great place. "
United States
John
The price is NZ$172
includes taxes & fees
12 Nov - 13 Nov
Freehand Chicago
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2719)
"Great place to stay "
United States
Larry William
The price is NZ$277
includes taxes & fees
7 Dec - 8 Dec
Hotel Riu Plaza Chicago
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (304)
"Perfect location! Tons of restaurants and shopping nearby! "
United States
MaryJane
The price is NZ$141
includes taxes & fees
7 Dec - 8 Dec
FOUND Hotel Chicago River North
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3.0 star property
8.4 out of 10, Very good, (1004)
"It was good. "
United States
Eimylin
The price is NZ$266
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn & Suites Chicago - Downtown by IHG
Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection
3.5 star property
8.2 out of 10, Very good, (3680)
"Loved the hotel and customer service."
United States
Whitney
The price is NZ$177
includes taxes & fees
23 Nov - 24 Nov
The Whitehall Hotel, BW Premier Collection
Lobby
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown
4.0 star property
9.4 out of 10, Exceptional, (2040)
"Great spot"
United States
Kirsten
Silversmith Hotel Chicago Downtown
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG
voco Chicago Downtown - Riverwalk by IHG
3.5 star property
8.8 out of 10, Excellent, (3321)
"Great stay!"
United States
Shanell
The price is NZ$185
includes taxes & fees
24 Nov - 25 Nov
voco Chicago Downtown - Riverwalk by IHG
Ballroom
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 star property
8.4 out of 10, Very good, (2068)
"Great hotel "
United States
Hicham
The price is NZ$272
includes taxes & fees
24 Nov - 25 Nov
Palmer House a Hilton Hotel
Pool
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8 out of 10, Excellent, (1698)
"Staff members was vey nice "
United States
Damonica
The price is NZ$172
includes taxes & fees
24 Nov - 25 Nov
Hilton Garden Inn Chicago Downtown South Loop
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

Our guide on where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
Downtown Chicago featuring 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

An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.

The Loop - Downtown which includes 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 a city and modern architecture

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Top Sleepy Hollow Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"."
Dominick 1-night trip
Posted 15 hours ago
InterContinental Chicago Magnificent Mile by IHG

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.