Search Hotels in Sleepy Hollow, 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
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Sleepy Hollow, Chicago

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, (2091)
"Great hotel"
The price is 4.193.965 ₫
4.923.295 ₫ total
includes taxes & fees
3 Nov - 4 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Reception
River Hotel
River Hotel
4.0 star property
8.8 out of 10, Excellent, (4746)
"Staff friendly and helpful..and accommodations just right..great location! "
The price is 4.190.445 ₫
4.919.165 ₫ total
includes taxes & fees
26 Oct - 27 Oct
River Hotel
Reception
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (3081)
"Very nice location and everything was a 10/10"
The price is 3.148.639 ₫
3.696.188 ₫ total
includes taxes & fees
13 Nov - 14 Nov
Eurostars 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, (2189)
"Great hotel "
The price is 4.193.965 ₫
5.820.308 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior
Hilton Chicago
Hilton Chicago
4.0 star property
8.4 out of 10, Very good, (2261)
"We loved this hotel it was beautiful and convenient . "
The price is 4.845.188 ₫
6.460.962 ₫ total
includes taxes & fees
13 Nov - 14 Nov
Hilton Chicago
Cocktail bar
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2867)
"Had a great stay!"
The price is 3.636.990 ₫
4.269.464 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Aloft Chicago Mag Mile
Banquet hall
Congress Plaza Hotel
Congress Plaza Hotel
3.5 star property
8.0 out of 10, Very good, (9416)
"Beautiful hotel!"
Congress Plaza Hotel
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, (1598)
"Great Hotel"
The price is 3.426.150 ₫
4.021.957 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Crowne Plaza Chicago West Loop by IHG
Terrace/patio
citizenM Chicago Downtown
citizenM Chicago Downtown
4.0 star property
9.2 out of 10, Wonderful, (3951)
"Great place to stay. "
The price is 3.449.645 ₫
4.049.537 ₫ total
includes taxes & fees
9 Nov - 10 Nov
citizenM Chicago Downtown
Ballroom
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 star property
8.8 out of 10, Excellent, (3107)
"Our stay was great"
The price is 3.785.896 ₫
4.444.263 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Hilton Chicago/Magnificent Mile Suites
Rooftop terrace
Best Western River North Hotel
Best Western River North Hotel
2.5 star property
7.8 out of 10, Good, (1026)
"Great stay"
The price is 2.665.808 ₫
3.129.392 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Best Western River North Hotel
Lobby
Regal Inn - Chicago O'Hare Airport
Regal Inn - Chicago O'Hare Airport
2.0 star property
8.0 out of 10, Very good, (1009)
"Inexpensive, close to the airport, clean"
Regal Inn - Chicago O'Hare Airport
Cocktail bar
Freehand Chicago
Freehand Chicago
4.0 star property
8.0 out of 10, Very good, (2472)
"Great place"
The price is 2.111.036 ₫
2.942.218 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Freehand Chicago
Lobby
Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
3.5 star property
7.6 out of 10, Good, (1476)
"Budget rate rooms - decent price and decent place to sleep"
The price is 2.015.316 ₫
2.276.904 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Super 8 by Wyndham Chicago O'Hare Airport
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, (4080)
"We definitely will stay there again place was very nice "
The price is 3.673.887 ₫
4.312.776 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior
Comfort Suites Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport
3.0 star property
8.2 out of 10, Very good, (2660)
"Clean quiet and great location!"
The price is 2.216.848 ₫
2.526.762 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Comfort Suites Chicago O'Hare Airport
Front of property – evening/night
Eaglewood Resort and Spa
Eaglewood Resort and Spa
4.0 star property
8.6 out of 10, Excellent, (1012)
"Beautiful property, reasonably priced for an end of season stay. "
The price is 3.036.096 ₫
3.949.297 ₫ total
includes taxes & fees
16 Oct - 17 Oct
Eaglewood Resort and Spa
Front of property
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4.0 star property
9.4 out of 10, Exceptional, (2602)
"Great place to stay "
The price is 3.727.751 ₫
5.118.693 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Hotel Riu Plaza Chicago
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, (3659)
"Great location , good breakfast"
The price is 2.583.844 ₫
3.033.175 ₫ total
includes taxes & fees
11 Nov - 12 Nov
The Whitehall Hotel, BW Premier Collection
Exterior
FOUND Hotel Chicago River North
FOUND Hotel Chicago River North
2.0 star property
8.2 out of 10, Very good, (274)
"Perfect location! Tons of restaurants and shopping nearby! "
The price is 2.118.152 ₫
2.486.498 ₫ total
includes taxes & fees
10 Nov - 11 Nov
FOUND Hotel Chicago River North
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile - River North

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

The Loop - Downtown featuring a river or creek

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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 featuring a city and modern architecture

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Top Sleepy Hollow Hotel Reviews

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.