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?

Hawthorne Works Museum, Jedlica Performing Arts Center, and Balzekas Museum of Lithuanian Culture are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Wintrust Sports Complex and Firehouse Community Arts Center of Chicago are also worth a stop.

Find hotels in Sleepy Hollow, Chicago from SAR 541

Where to?

Dates

May 2026

5

June 2026

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

Our top choices for Sleepy Hollow hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 14.4 km from Sleepy Hollow

Mark

SAR 971 total

includes taxes & fees

26 May - 27 May

The Wade

Streeterville, 13.8 km from Sleepy Hollow

Nuria

SAR 754 total

includes taxes & fees

26 May - 27 May

Sheraton Grand Chicago Riverwalk

Streeterville, 13.2 km from Sleepy Hollow

Grisel

SAR 1,110 total

includes taxes & fees

9 May - 10 May

Swissotel - Chicago

13 km from Sleepy Hollow

Lorena

SAR 1,050 total

includes taxes & fees

8 May - 9 May

DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Claire

SAR 720 total

includes taxes & fees

25 May - 26 May

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Darin

SAR 803 total

includes taxes & fees

10 May - 11 May

Fairmont Chicago at Millennium Park

The Loop, 12.9 km from Sleepy Hollow

Nicole

SAR 902 total

includes taxes & fees

8 May - 9 May

Aloft Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Fedna

SAR 665 total

includes taxes & fees

10 May - 11 May

Ivy Boutique Hotel

Streeterville, 13.4 km from Sleepy Hollow

Manjeet

SAR 560 total

includes taxes & fees

26 May - 27 May

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Streeterville, 13.9 km from Sleepy Hollow

Yuge

SAR 656 total

includes taxes & fees

10 May - 11 May

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Angela

SAR 598 total

includes taxes & fees

10 May - 11 May

Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Judith Daniella

SAR 716 total

includes taxes & fees

20 May - 21 May

Millennium Hotel Knickerbocker Chicago

Streeterville, 13.8 km from Sleepy Hollow

Hamit

SAR 611 total

includes taxes & fees

10 May - 11 May

Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Jennifer

SAR 1,115 total

includes taxes & fees

24 May - 25 May

Hyatt Centric Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Shannon

SAR 865 total

includes taxes & fees

25 May - 26 May

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

Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Lateia

SAR 722 total

includes taxes & fees

10 May - 11 May

The Chicago Hotel Collection - Magnificent Mile

Streeterville, 13.5 km from Sleepy Hollow

Dwight Demond

SAR 541 total

includes taxes & fees

10 May - 11 May

Hampton Inn Chicago Downtown/Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Devona

SAR 716 total

includes taxes & fees

11 May - 12 May

Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Nichole

SAR 706 total

includes taxes & fees

27 May - 28 May

Congress Plaza Hotel

The Loop, 11.9 km from Sleepy Hollow

Matthew

SAR 559 total

includes taxes & fees

8 May - 9 May

View all properties

Where to stay in Sleepy Hollow

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

Downtown Chicago

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

See properties

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

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

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

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

Hotel Felix River North/Magnificent Mile

10/10 Excellent

"The hotel Felix was perfect . Walking distance to everything I wanted to do . Friendly staff and great accommodations."

Hotel Riu Plaza Chicago

10/10 Excellent

"Every single person we came in contact with were very kind and respectful. The hotel was clean, quiet, and very centrally located to everything. A big shout out to the bellman/concierge guys on Monday afternoon at around 3:30 pm. My husband dropped some cash on the floor and they came to find us outside to see if we were the ones who dropped it. I think one was Ruiz and I can't remember the name of the other gentleman. We had a lovely time and I would definitely come back again."

The Chicago Hotel Collection - Magnificent Mile

4/10 Poor

"I chose this hotel for my business stay because it offered early check-in and late checkout. I called the hotel days prior to my stay to confirm my late checkout would be available. The staff member was very cold over the phone but did confirm this for me. My early check in was granted and there was no mention of any issues from the staff or what time I need to checkout. I received a call the next day at 1:30pm that I need to be out of y room immediately. They also charged me a late checkout fee with no prior notice or warning. I should’ve listened to the reviews of this hotel. They clearly only want your money and will do anything to get you to pay more than the room price."

Hilton Chicago/Magnificent Mile Suites

4/10 Poor

"You had to run the shower, the bathroom faucet, and the one in the room to get the hot water to turn on. The toilets throughout the hotel did not flush well. We had to call maintenance multiple times to.plunge the toilet and the toilet in the lobby had to be flushed multiple times just for tissue to go down for a number 1. The staff was definitely friendly and that was a plus and only plus."

Fairmont Chicago at Millennium Park

6/10 Okay

"It's ok, no rats or cockroaches but did I expect better for the price? Yes. And don't be fooled, there are hidden fees, something called a "city resort tax" or something like that (even though it's not a resort--no perks), that you'll be charged additional for at the hotel, no matter what Expedia says about fees and taxes being included in the price."

Find hotels in Sleepy Hollow, Chicago from SAR 541

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

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 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

Hampton Inn Chicago Downtown/Magnificent Mile

Hotel Riu Plaza Chicago

Congress Plaza Hotel

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Hotel Felix River North/Magnificent Mile

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