Top Sleepy Hollow Hotels

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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

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Always a delight to stay at the Intercontinental in Chicago! The staff is professional and friendly, the rooms are clean and well maintained. Also, the location is ideal."

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent

"This is a beautiful hotel and wonderful staff. We loved the design and the decor. The coffee area was so well set up and very thoughtful with honey, almond milk, lemons for water and tea. Very clean and delicious. The gym was a bit small but had all of the equipment and weights needed. They had chilled eucalyptus face towels that I loved so much at the end of my workout. The location was great. We loved the Nederlander theater and seeing The Notebook! My husband and I had an amazing time. Chicago was great! This hotel will not disappoint."

Hyatt Regency Chicago

10/10 Excellent

"We stayed at the Hyatt Regency Chicago, and when I tell you this hotel is HUGE, I mean HUGE! There are different towers, so it can take a minute to figure out where you’re going. Check-in is upstairs, not on the main level. The hotel has several restaurants, and I recommend making reservations, especially on busy weekends. We received a $25 nightly credit that could be used at participating restaurants during certain evening hours, but not at the Market. Our room was clean and comfortable. I stayed on the 20th floor with a beautiful river view. I could hear some music from the boats below, but it wasn’t loud enough to disturb my sleep. My mother was on the 30th floor and didn’t hear anything. Transportation is convenient with taxis outside, easy access to Ubers and a car rental location inside the hotel. There are also nice sitting areas with city views, charging stations and fireplaces. Everyone was nice, but Camille at the front desk was especially helpful and accommodating. I’m very particular about hotel cleanliness, and this room passed my cleanliness check! My only complaint was the bed, which was uncomfortable and sank in the middle. Overall, it’s pricey, but we enjoyed our stay. The location is a BIG plus, with Michigan Avenue, restaurants and attractions within walking distance."

Hyatt Regency O'Hare Chicago

10/10 Excellent

"This hotel is absolutely beautiful! And just across the street from the convention center! Our room was spotless, so clean and tidy. The restaurant serves an amazing breakfast buffet for under $30 per person.... well worth it for the variety and quality of the food. My only contention is that you have to pay for parking ($45 per night) which I've never ever heard of in the 50 years of my life. Apparently, most hotels in Chicago don't own their parking lots. They are owned by a separate company who collects their fees thru the hotel. For that reason alone I'm not sure i ever want to stay in Chicago again. I can find a million other places to visit that don't charge extra to park at the hotel. Otherwise, this hotel is very nice and clean and in an excellent location."

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 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.

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Our top choices for Sleepy Hollow hotels

1. Hyatt House Chicago/West Loop-Fulton Market

2. Holiday Inn & Suites Chicago - Downtown by IHG

3. Crowne Plaza Chicago West Loop by IHG

4. The Emily Hotel

5. Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area

6. The Buckingham Hotel

7. Hilton Garden Inn Chicago Central Loop

8. Canopy by Hilton Chicago Central Loop

9. Best Western Grant Park Hotel

10. Level Chicago Fulton Market

11. La Quinta Inn & Suites by Wyndham Chicago Downtown

12. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

13. Le Méridien Essex Chicago

14. Hilton Chicago

15. Homewood Suites by Hilton Chicago Downtown South Loop

16. Hyatt Place Chicago/Downtown - The Loop

17. Hilton Garden Inn Chicago Downtown South Loop

18. Club Quarters Hotel, Central Loop, Chicago

19. Travelodge by Wyndham Downtown Chicago

20. Hyatt Centric The Loop Chicago

Where to stay in Sleepy Hollow

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

Frequently asked questions