Hotels in Sleepy Hollow, Chicago

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
11 Jul - 12 Jul
Tomorrow
12 Jul - 13 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Filter by

Guest rating
Guest rating
Property class

Top 10 Hotels in Sleepy Hollow, Chicago

The Buckingham Hotel
Lounge

The Buckingham Hotel

3.5 star property
9.0 out of 10, Wonderful, (1003)
"Great location, very clean, spacious, friendly staff."
The Buckingham Hotel
Hyatt Place Chicago/River North
Free daily on-the-go breakfast

Hyatt Place Chicago/River North

3.5 star property
9.2 out of 10, Wonderful, (1435)
"Great staff and amazing location "
The price is RM849
RM997 total
includes taxes & fees
10 Aug - 11 Aug
Hyatt Place Chicago/River North
Thompson Chicago, by Hyatt
Restaurant

Thompson Chicago, by Hyatt

4.5 star property
9.0 out of 10, Wonderful, (1160)
"Great location and property!"
The price is RM588
RM815 total
includes taxes & fees
10 Aug - 11 Aug
Thompson Chicago, by Hyatt
Hyatt Regency Chicago
2 bars/lounges

Hyatt Regency Chicago

4.0 star property
9.2 out of 10, Wonderful, (3290)
"Great location and stay"
The price is RM989
RM1,285 total
includes taxes & fees
6 Aug - 7 Aug
Hyatt Regency Chicago
Central Loop Hotel
Breakfast, lunch, dinner served; American cuisine

Central Loop Hotel

4.0 star property
8.6 out of 10, Excellent, (1802)
"Amazing welcome from staff and very convenient restaurant in the lobby area. "
The price is RM696
RM816 total
includes taxes & fees
24 Jul - 25 Jul
Central Loop Hotel
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2755)
"Staff was very friendly and efficient from the valet to the front desk. Good location id stay there again"
The price is RM760
RM892 total
includes taxes & fees
6 Aug - 7 Aug
Aloft Chicago Mag Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2057)
"Amazing property clean comfy bedding and wonderful views"
The price is RM955
RM1,245 total
includes taxes & fees
13 Jul - 14 Jul
Sable at Navy Pier Chicago, Curio Collection by Hilton
River Hotel
Lobby

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4355)
"The hotel was great from the staff to the location "
The price is RM671
RM788 total
includes taxes & fees
24 Jul - 25 Jul
River Hotel
Arlo Chicago
Exterior

Arlo Chicago

4.0 star property
9.2 out of 10, Wonderful, (1787)
"Been there a couple times always a nice stay, great location "
The price is RM825
RM1,093 total
includes taxes & fees
13 Jul - 14 Jul
Arlo Chicago
Hilton Chicago/Magnificent Mile Suites
Restaurant

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2426)
"Friendly staff, beautiful views, excellent location "
The price is RM719
RM844 total
includes taxes & fees
10 Aug - 11 Aug
Hilton Chicago/Magnificent Mile Suites
La Quinta by Wyndham Chicago O'Hare Airport
Free daily buffet breakfast

La Quinta by Wyndham Chicago O'Hare Airport

3.0 star property
8.4 out of 10, Very good, (1648)
"Very new hotel with a Great breakfast"
The price is RM408
RM465 total
includes taxes & fees
11 Aug - 12 Aug
La Quinta by Wyndham Chicago O'Hare Airport
Ohio House Motel
Reception

Ohio House Motel

2.5 star property
9.0 out of 10, Wonderful, (1014)
"Great place to stay!"
The price is RM523
RM614 total
includes taxes & fees
4 Aug - 5 Aug
Ohio House Motel
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1778)
"Love this hotel"
The price is RM747
RM983 total
includes taxes & fees
8 Aug - 9 Aug
Palmer House a Hilton Hotel
Level Chicago - River North
Premium bedding, pillow-top beds, in-room safe, individually furnished

Level Chicago - River North

4.0 star property
9.0 out of 10, Wonderful, (640)
"Great place "
The price is RM1,188
RM1,489 total
includes taxes & fees
11 Aug - 12 Aug
Level Chicago - River North
L7 Chicago by LOTTE
Exterior

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (2625)
"Very nice location and great restaurant on the premises "
The price is RM942
RM1,106 total
includes taxes & fees
27 Jul - 28 Jul
L7 Chicago by LOTTE
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (1886)
"Great stay! "
The price is RM581
RM682 total
includes taxes & fees
10 Aug - 11 Aug
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hotel Felix River North/Magnificent Mile
Lobby sitting area

Hotel Felix River North/Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (1854)
"Great location "
The price is RM799
RM1,067 total
includes taxes & fees
21 Jul - 22 Jul
Hotel Felix River North/Magnificent Mile
Sonesta Simply Suites Chicago O'Hare Airport
Fridge, microwave, stovetop, dishwasher

Sonesta Simply Suites Chicago O'Hare Airport

2.0 star property
8.4 out of 10, Very good, (1818)
"Very comfortable stay. "
The price is RM436
RM497 total
includes taxes & fees
24 Jul - 25 Jul
Sonesta Simply Suites Chicago O'Hare Airport
The Willows Hotel
Premium bedding, minibar, desk, blackout curtains

The Willows Hotel

3.0 star property
8.4 out of 10, Very good, (1008)
"Great stay"
The price is RM567
RM665 total
includes taxes & fees
11 Aug - 12 Aug
The Willows Hotel
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1864)
"great stay!"
Silversmith Hotel Chicago Downtown
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.

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 map

Downtown Chicago

5 out of top 10 points of interest in this area

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 map

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 map

The Loop

Michigan Avenue and Art Institute of Chicago 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 map

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.

Lincoln Park showing modern architecture and a city
Lincoln Park map

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.

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?

Places you might want to visit in the area around Sleepy Hollow include Hawthorne Works Museum and Balzekas Museum of Lithuanian Culture. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.