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

Ashraf

SAR 942 total

includes taxes & fees

8 Sep - 9 Sep

2. The Wade

Streeterville, 13.8 km from Sleepy Hollow

Allison

SAR 643 total

includes taxes & fees

7 Sep - 8 Sep

3. Sheraton Grand Chicago Riverwalk

Streeterville, 13.2 km from Sleepy Hollow

PHIL

SAR 1,380 total

includes taxes & fees

7 Sep - 8 Sep

4. Swissotel - Chicago

13 km from Sleepy Hollow

Bridgette

SAR 1,059 total

includes taxes & fees

8 Sep - 9 Sep

Outdoor pool, cabanas (surcharge), pool umbrellas

5. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Tonya

SAR 751 total

includes taxes & fees

8 Sep - 9 Sep

6. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Valerie

SAR 936 total

includes taxes & fees

10 Sep - 11 Sep

7. Radisson Blu Aqua Hotel Chicago

12.9 km from Sleepy Hollow

Marlon

SAR 1,228 total

includes taxes & fees

7 Sep - 8 Sep

8. Fairmont Chicago at Millennium Park

The Loop, 12.9 km from Sleepy Hollow

Michael

SAR 1,022 total

includes taxes & fees

8 Sep - 9 Sep

9. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Odessia

SAR 687 total

includes taxes & fees

7 Sep - 8 Sep

10. Ivy Boutique Hotel

Streeterville, 13.4 km from Sleepy Hollow

Jerry

SAR 670 total

includes taxes & fees

7 Sep - 8 Sep

11. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Streeterville, 13.9 km from Sleepy Hollow

Kelly

SAR 700 total

includes taxes & fees

7 Sep - 8 Sep

12. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Marissa

SAR 576 total

includes taxes & fees

7 Sep - 8 Sep

13. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Jeremy

SAR 709 total

includes taxes & fees

8 Sep - 9 Sep

14. Millennium Hotel Knickerbocker Chicago

Streeterville, 13.8 km from Sleepy Hollow

Vijay

SAR 772 total

includes taxes & fees

20 Sep - 21 Sep

15. Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Jerry

SAR 1,223 total

includes taxes & fees

7 Sep - 8 Sep

16. Hyatt Centric Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Sara

SAR 1,045 total

includes taxes & fees

7 Sep - 8 Sep

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

17. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Jyothi Swaroop

SAR 737 total

includes taxes & fees

7 Sep - 8 Sep

18. The Chicago Hotel Collection - Magnificent Mile

Streeterville, 13.5 km from Sleepy Hollow

Colten

SAR 479 total

includes taxes & fees

7 Sep - 8 Sep

19. Hotel Saint Clair- Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

LuShana

SAR 507 total

includes taxes & fees

7 Sep - 8 Sep

20. Hampton Inn Chicago Downtown/Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Jon

SAR 732 total

includes taxes & fees

7 Sep - 8 Sep

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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 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 Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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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 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.

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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

Hotel Saint Clair- Magnificent Mile

10/10 Excellent

"Very nice location"

Congress Plaza Hotel

8/10 Good

"I can see why this place is rated 8/10. I would agree with that overall. Some pros: it is excellent for location, as it is in a prime area of the city, close to a lot of sites and accessible by transit. We didn't drive but parking is a nightmare in Chicago. I wouldn't blame the hotel for that. The room was very spacious, huge ceilings, giant closet, comfortable bed, lots of windows, renovated, and clean. It is a very nice, art-deco style of building, well maintained with some old charm. The cons: the light woke us up every day, as there were no internal curtains, just decorative ones. This needs to be changed immediately. Also, there was no climate control. It was either on or off. You could control the fan speed but that's it. A lot of people complained that the toilet was running. Ours wasn't. The room got noisy at times but that's also not the hotel's fault, as we faced a main road. Keep that in mind while choosing a room. The staff weren't overly friendly but were professional and seemed helpful. For what we paid, it was well-worth the price, as Chicago can get very expensive. Kanye West happened to be performing there for two of the three nights we were there. I think we booked before this announcement or we would've had to pay triple. So, we can't really complain about value."

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.

Find hotels in Sleepy Hollow, Chicago

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Our top choices for Sleepy Hollow hotels

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

2. The Wade

3. Sheraton Grand Chicago Riverwalk

4. Swissotel - Chicago

5. DoubleTree by Hilton Chicago - Magnificent Mile

6. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

7. Radisson Blu Aqua Hotel Chicago

8. Fairmont Chicago at Millennium Park

9. Aloft by Marriott Chicago Mag Mile

10. Ivy Boutique Hotel

11. Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

12. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

13. Hilton Chicago/Magnificent Mile Suites

14. Millennium Hotel Knickerbocker Chicago

15. Hyatt Regency Chicago

16. Hyatt Centric Chicago Magnificent Mile

17. Courtyard by Marriott Chicago Magnificent Mile

18. The Chicago Hotel Collection - Magnificent Mile

19. Hotel Saint Clair- Magnificent Mile

20. Hampton Inn Chicago Downtown/Magnificent Mile

Where to stay in Sleepy Hollow

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Hotel Saint Clair- Magnificent Mile

Frequently asked questions