Top Sleepy Hollow Hotels

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Our top choices for Sleepy Hollow hotels

1. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

LISA

₩363,277 total

includes taxes & fees

Sep 27 - Sep 28

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

Streeterville, 14.4 km from Sleepy Hollow

Shanequa

₩513,876 total

includes taxes & fees

Sep 27 - Sep 28

3. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Brian

₩335,456 total

includes taxes & fees

Sep 27 - Sep 28

Outdoor pool, cabanas (surcharge), pool umbrellas

4. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Madelyn

₩353,871 total

includes taxes & fees

Sep 21 - Sep 22

5. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Streeterville, 13.9 km from Sleepy Hollow

Kelly

₩318,378 total

includes taxes & fees

Sep 30 - Oct 1

6. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Shweta

₩358,655 total

includes taxes & fees

Sep 27 - Sep 28

7. River Hotel

The Loop, 12.7 km from Sleepy Hollow

Isabella

₩282,564 total

includes taxes & fees

Sep 20 - Sep 21

55-inch LCD TV with cable channels, TV, pay movies

8. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Andrea

₩416,118 total

includes taxes & fees

Sep 21 - Sep 22

9. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.6 km from Sleepy Hollow

Mythli

₩371,531 total

includes taxes & fees

Sep 20 - Sep 21

10. Hampton Inn Chicago-O'Hare International Airport

19.4 km from Sleepy Hollow

karen

₩214,401 total

includes taxes & fees

Sep 30 - Oct 1

11. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Terri

₩364,929 total

includes taxes & fees

Sep 27 - Sep 28

12. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Phillip

₩279,328 total

includes taxes & fees

Sep 20 - Sep 21

13. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Mya

₩443,102 total

includes taxes & fees

Oct 13 - Oct 14

14. Hyatt Centric The Loop Chicago

Theatre District, 11.8 km from Sleepy Hollow

Tamika

₩363,674 total

includes taxes & fees

Sep 20 - Sep 21

15. The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 13.9 km from Sleepy Hollow

Michael T.

₩250,945 total

includes taxes & fees

Sep 30 - Oct 1

16. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

Ann

₩410,569 total

includes taxes & fees

Oct 14 - Oct 15

Suite, 1 Bedroom, Corner | Private kitchen | Coffee/tea maker, full-size fridge, microwave, stovetop

17. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Pramukha

₩398,613 total

includes taxes & fees

Sep 27 - Sep 28

18. citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

Isayra

₩328,602 total

includes taxes & fees

Sep 20 - Sep 21

19. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Sara

₩340,342 total

includes taxes & fees

Sep 27 - Sep 28

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Melissa

₩418,326 total

includes taxes & fees

Sep 27 - Sep 28

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Where to stay in Sleepy Hollow

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

A cityscape with tall skyscrapers and a historic tower.

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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A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

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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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.

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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.

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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.

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Top Sleepy Hollow Hotel Reviews

Congress Plaza Hotel

10/10 Excellent

"F"

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"liked the location of the hotel, room was nice, the restaurant in the hotel adds to the convenience of the property. I did not like EXPEDIA adding extra charges to my bill tried to get them removed but I couldn't get on web site in order to do it. I did not order the insurance and was charged, next trip I will make sure I don't use Expedias web site."

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

8/10 Good

"There were a couple of things about this hotel that threw me for a loop (no in room coffee machine -- but plenty of coffee at the bar with choice of skim, half and half and cream; you first encounter the bar versus the registration area), but I would definitely stay here again, and for that I compliment the staff. Fatima greeted us at check in and immediately noticed my daughter had mobility issues and offered to change our room for an accessible one. Since this was my first overnight trip with my daughter I hadn't even thought of that! I appreciated that she saw a way to make our stay better and made it happen. Fatima also always had a smile on her face when we saw her and was always ready to answer any question. I didn't get the name of the doorman we interacted with the most (but I did get a photo with him!), which I regret. He was an older many who worked day shift and he touched my heart when he stayed by my daughter while I went to get our car from the parking garage. He didn't have to do that. The people definitely made this staff wonderful!"

Frequently asked questions

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

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Our top choices for Sleepy Hollow hotels

1. Hyatt Place Chicago/Downtown - The Loop

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

3. Hilton Chicago/Magnificent Mile Suites

4. DoubleTree by Hilton Chicago - Magnificent Mile

5. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

6. Embassy Suites by Hilton Chicago Downtown River North

7. River Hotel

8. L7 Chicago by LOTTE

9. La Quinta Inn & Suites by Wyndham Chicago Downtown

10. Hampton Inn Chicago-O'Hare International Airport

11. Hyatt Place Chicago/River North

12. Crowne Plaza Chicago West Loop by IHG

13. Hotel Riu Plaza Chicago

14. Hyatt Centric The Loop Chicago

15. The Chicago Hotel Collection Ambassador Gold Coast

16. Hilton Vacation Club Hotel Blake Chicago

17. Homewood Suites by Hilton Chicago Downtown South Loop

18. citizenM Chicago Downtown

19. Best Western Grant Park Hotel

20. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Congress Plaza Hotel

Frequently asked questions

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