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?

Douglas Park, Hawthorne Works Museum, and Jedlica Performing Arts Center are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Los Globos and Balzekas Museum of Lithuanian Culture are also worth a stop.

Top Sleepy Hollow Hotels from SAR 690

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

Tomorrow

This weekend

Next weekend

Our top choices for Sleepy Hollow hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 14.4 km from Sleepy Hollow

Julie

SAR 1,142 total

includes taxes & fees

17 Aug - 18 Aug

The Wade

Streeterville, 13.8 km from Sleepy Hollow

Richard

SAR 1,335 total

includes taxes & fees

9 Aug - 10 Aug

Sheraton Grand Chicago Riverwalk

Streeterville, 13.2 km from Sleepy Hollow

Leigh Lynne

SAR 1,335 total

includes taxes & fees

16 Aug - 17 Aug

Swissotel - Chicago

13 km from Sleepy Hollow

SAR 1,213 total

includes taxes & fees

26 Jul - 27 Jul

Outdoor pool, cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Marianne

SAR 861 total

includes taxes & fees

9 Aug - 10 Aug

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Michael

SAR 1,058 total

includes taxes & fees

11 Aug - 12 Aug

Fairmont Chicago at Millennium Park

The Loop, 12.9 km from Sleepy Hollow

Haidar

SAR 1,558 total

includes taxes & fees

9 Aug - 10 Aug

Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Sonyce

SAR 804 total

includes taxes & fees

19 Jul - 20 Jul

Ivy Boutique Hotel

Streeterville, 13.4 km from Sleepy Hollow

Andrew

SAR 810 total

includes taxes & fees

10 Aug - 11 Aug

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Streeterville, 13.9 km from Sleepy Hollow

Sally

SAR 822 total

includes taxes & fees

9 Aug - 10 Aug

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Jeffrey

SAR 755 total

includes taxes & fees

19 Jul - 20 Jul

Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Chameka

SAR 777 total

includes taxes & fees

16 Aug - 17 Aug

Millennium Hotel Knickerbocker Chicago

Streeterville, 13.8 km from Sleepy Hollow

Lawrence

SAR 848 total

includes taxes & fees

16 Aug - 17 Aug

Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Kristen

SAR 1,313 total

includes taxes & fees

9 Aug - 10 Aug

Hyatt Centric Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Paul

SAR 996 total

includes taxes & fees

9 Aug - 10 Aug

Premium bedding, in-room safe, desk, blackout drapes

Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Zachary

SAR 960 total

includes taxes & fees

16 Aug - 17 Aug

The Chicago Hotel Collection - Magnificent Mile

Streeterville, 13.5 km from Sleepy Hollow

Precious

SAR 690 total

includes taxes & fees

27 Jul - 28 Jul

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Ivan

SAR 1,132 total

includes taxes & fees

16 Aug - 17 Aug

Hampton Inn Chicago Downtown/Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Tushar

SAR 802 total

includes taxes & fees

19 Jul - 20 Jul

Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Jessica

SAR 1,040 total

includes taxes & fees

9 Aug - 10 Aug

View all properties

Where to stay in Sleepy Hollow

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

A busy city street with tall buildings, a bus, and cars.

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.

See properties

A historic castle-like building with intricate stonework and a paved walkway.

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.

See properties

A river with yellow boats, a bridge, and tall buildings.

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.

See properties

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

See properties

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

See properties

Top Sleepy Hollow Hotel Reviews

Omni Chicago Hotel

10/10 Excellent

"Fantastic!"

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"This was a great place to stay for a quick weekend trip. This was convenient to get to off the interstate and was so convenient to walk to all the shops along magnificent mile. Raymond was such a bright welcoming and the two valet drivers were great as well. They even let me keep my vehicle parked later than check out so we could explore some more of the city before we left town. I would stay here again. I wish we could have made it up to the rooftop bar but timing wasn’t our friend. Rooms were slightly outdated and I’ve stayed at places with softer sheets but I’m easy to please!"

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"This property and staff was amazing! We planned a small event for my daughters marriage proposal in one of their lounges as well as stayed in one of the rooms. The staff was so appreciatively attentive to our needs to pull off the proposal as a secret. My family felt they went above and beyond when they attended to us during our small event. Because of a plane delay we were scrambling to get things set up, they recognized that and stepped right in to help wherever they could including bringing much needed refreshing glasses of water since we were hot, scrambling and parched. Three families including my husband and I stayed at the Allegro. This hotel is iconic, historic and absolutely beautiful. Our room offered everything we needed: was clean and the mattress was great. All staff from doorman to check-out was very kind and helpful, including the Allegro Lounge with great service and drinks. If we have opportunity to stay in Chicago again we will be staying here."

Find hotels in Sleepy Hollow, Chicago from SAR 690

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sleepy Hollow hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

Sheraton Grand Chicago Riverwalk

Swissotel - Chicago

DoubleTree by Hilton Chicago - Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Fairmont Chicago at Millennium Park

Aloft by Marriott Chicago Mag Mile

Ivy Boutique Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Millennium Hotel Knickerbocker Chicago

Hyatt Regency Chicago

Hyatt Centric Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

Homewood Suites by Hilton Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

Hotel Riu Plaza Chicago

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Omni Chicago Hotel

Explore a world of travel with Expedia

Frequently asked questions

Hotels in top Chicago neighborhoods

Hotels near popular Chicago Attractions

More Accommodation Types in Sleepy Hollow

Explore more hotels