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

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Our top choices for Sleepy Hollow hotels

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 14.4 km from Sleepy Hollow

Deborah

NT$9,112 total

includes taxes & fees

Jun 30 - Jul 1

2. Omni Chicago Hotel

Streeterville, 13.2 km from Sleepy Hollow

Bruce

NT$5,835 total

includes taxes & fees

Jul 1 - Jul 2

3. Congress Plaza Hotel

The Loop, 11.9 km from Sleepy Hollow

Felipa

NT$5,112 total

includes taxes & fees

Jun 29 - Jun 30

4. Palmer House a Hilton Hotel

Theatre District, 12.1 km from Sleepy Hollow

Charles Otto

NT$9,364 total

includes taxes & fees

Jul 1 - Jul 2

5. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Corey

NT$6,916 total

includes taxes & fees

Jul 6 - Jul 7

6. Travelodge by Wyndham Downtown Chicago

The Loop, 11.8 km from Sleepy Hollow

Ming

NT$5,083 total

includes taxes & fees

Jul 1 - Jul 2

7. Staypineapple, An Iconic Hotel, The Loop

Theatre District, 12.2 km from Sleepy Hollow

Debby

NT$6,164 total

includes taxes & fees

Jul 6 - Jul 7

8. Swissotel - Chicago

13 km from Sleepy Hollow

Martha

NT$7,733 total

includes taxes & fees

Jul 1 - Jul 2

9. Silversmith Hotel Chicago Downtown

Theatre District, 12.2 km from Sleepy Hollow

Gabino

NT$6,255 total

includes taxes & fees

Jul 5 - Jul 6

10. The Blackstone, Autograph Collection

The Loop, 11.8 km from Sleepy Hollow

Neydee

NT$6,766 total

includes taxes & fees

Jul 6 - Jul 7

2 restaurants; breakfast, lunch, and dinner served

11. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.7 km from Sleepy Hollow

Robert

NT$8,883 total

includes taxes & fees

Jul 1 - Jul 2

12. Eurostars Magnificent Mile

River North, 13 km from Sleepy Hollow

Audrey

NT$5,415 total

includes taxes & fees

Jul 2 - Jul 3

13. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Alexandra

NT$4,483 total

includes taxes & fees

Jul 1 - Jul 2

14. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Avradita

NT$6,014 total

includes taxes & fees

Jun 30 - Jul 1

15. The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 13.9 km from Sleepy Hollow

Zhiwen

NT$5,878 total

includes taxes & fees

Jul 1 - Jul 2

16. Sheraton Grand Chicago Riverwalk

Streeterville, 13.2 km from Sleepy Hollow

Pamela

NT$8,618 total

includes taxes & fees

Jul 5 - Jul 6

17. Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Marianne

NT$10,154 total

includes taxes & fees

Jul 2 - Jul 3

18. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Justin

NT$6,326 total

includes taxes & fees

Jul 6 - Jul 7

Presidential Suite, 1 Bedroom, Non Smoking | Premium bedding, in-room safe, desk, blackout drapes

19. Hotel 55 Chicago Downtown

River North, 13.1 km from Sleepy Hollow

Matt

NT$6,241 total

includes taxes & fees

Jul 1 - Jul 2

20. Fairmont Chicago at Millennium Park

The Loop, 12.9 km from Sleepy Hollow

Mohammed Izzal

NT$8,744 total

includes taxes & fees

Jul 6 - Jul 7

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

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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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.

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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.

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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.

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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.

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Top Sleepy Hollow Hotel Reviews

Travelodge by Wyndham Downtown Chicago

10/10 Excellent

"Easy access to everything"

Crowne Plaza Chicago West Loop by IHG

6/10 Okay

"Received a message from the hotel in advance that, among other details, parking is available in the garage across the courtyard. Arrived, pulled into garage and into a hotel designated spot in the garage. But at check-in was told all hotel spots were reserved, no more were available, and I needed to move my vehicle. There was no such detail in the advance information -- and it seems pretty important. Also, there was no way to lock/secure the bathroom door."

Freehand Chicago

6/10 Okay

"I haven't stayed at a hotel/hostel before, so I don't know if my expectations were unreasonable. First, the good. The staff were friendly and helpful. The location was perfect. The hot water and AC were plentiful. I felt safe and wasn't bothered by noise from neighbors. I didn't see any bugs. They even had a live musician during at least one of the evenings I was there. Now the bad. We had a private quad. It was dirty. The walls, some of the bedding, the bunk bed curtains were stained and gross. We found trash from the previous guests. There was so much dust and debris, especially in the part of the bunks that held the mattresses. The shower curtain and tiles were moldy. The room needed a good scrubbing and a fresh coat of paint. I wouldn't stay there again unless they improved their housekeeping."

Find hotels in Sleepy Hollow, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Sleepy Hollow hotels

1. Sable at Navy Pier Chicago, Curio Collection by Hilton

2. Omni Chicago Hotel

3. Congress Plaza Hotel

4. Palmer House a Hilton Hotel

5. Hotel Riu Plaza Chicago

6. Travelodge by Wyndham Downtown Chicago

7. Staypineapple, An Iconic Hotel, The Loop

8. Swissotel - Chicago

9. Silversmith Hotel Chicago Downtown

10. The Blackstone, Autograph Collection

11. LondonHouse Chicago, Curio Collection by Hilton

12. Eurostars Magnificent Mile

13. Best Western Grant Park Hotel

14. Hilton Chicago/Magnificent Mile Suites

15. The Chicago Hotel Collection Ambassador Gold Coast

16. Sheraton Grand Chicago Riverwalk

17. Hyatt Regency Chicago

18. Hilton Garden Inn Chicago Downtown South Loop

19. Hotel 55 Chicago Downtown

20. Fairmont Chicago at Millennium Park

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Travelodge by Wyndham Downtown Chicago

Frequently asked questions

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