Top 10 Sleepy Hollow Hotels of 2026

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Our top choices for Sleepy Hollow hotels

A brick building with a restaurant named "BARCLAYS" and a sign for "THE COTTAGE OF OAK BURTON."

1. Carleton of Oak Park

9.6 km from Sleepy Hollow

Brad

includes taxes & fees

9 Nov - 10 Nov

A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

2. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Georgianna

includes taxes & fees

23 Nov - 24 Nov

A modern hotel lobby with seating areas, a reception desk, and an elevator.

3. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Michelle

includes taxes & fees

24 Nov - 25 Nov

An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

4. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Aran

includes taxes & fees

24 Nov - 25 Nov

A modern kitchen with a large window, a dining area, and a view of the sea.

5. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Nicole

includes taxes & fees

23 Nov - 24 Nov

A modern living room with a sofa, armchairs, a coffee table, and a bookshelf.

6. Le Méridien Essex Chicago

The Loop, 11.6 km from Sleepy Hollow

Caitlin Vania

includes taxes & fees

24 Nov - 25 Nov

A modern hotel with a glass facade, a waterfront location, and a large Ferris wheel in the background.

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

Streeterville, 14.4 km from Sleepy Hollow

Bonnie

includes taxes & fees

22 Nov - 23 Nov

A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.

8. Level Chicago Fulton Market

West Loop, 11.5 km from Sleepy Hollow

Trang

includes taxes & fees

22 Nov - 23 Nov

A modern hotel with a glass facade, multiple floors, and a visible entrance.

9. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

Cordula

includes taxes & fees

24 Nov - 25 Nov

A multi-story hotel with a prominent sign reading "Crowne Plaza."

10. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Chriselda

includes taxes & fees

25 Nov - 26 Nov

A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.

11. Congress Plaza Hotel

The Loop, 11.9 km from Sleepy Hollow

Ashya

includes taxes & fees

22 Nov - 23 Nov

A modern hotel lobby with a bar area, seating arrangements, and a television screen.

12. Cambria Hotel Chicago Loop - Theatre District

Theatre District, 12.2 km from Sleepy Hollow

Vansh

includes taxes & fees

24 Nov - 25 Nov

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

13. Hampton Inn & Suites Chicago Downtown

River North, 12.7 km from Sleepy Hollow

Tracy

includes taxes & fees

24 Nov - 25 Nov

A modern building with a colorful facade and a red circular seating area.

14. citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

Katarina

includes taxes & fees

23 Nov - 24 Nov

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

15. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

tahira

includes taxes & fees

24 Nov - 25 Nov

The Claridge House building with a sign, American and another flag, and outdoor seating with umbrellas.

16. Claridge House Chicago, Tapestry Collection by Hilton

13.8 km from Sleepy Hollow

Scott

includes taxes & fees

22 Nov - 23 Nov

A multi-story hotel with a prominent 'La Quinta' sign, featuring a modern architectural design with large windows and a flat facade.

17. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.6 km from Sleepy Hollow

Andres

includes taxes & fees

24 Nov - 25 Nov

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

18. Hampton Inn Chicago West Loop Fulton Market Area

11.4 km from Sleepy Hollow

Peggy.

includes taxes & fees

25 Nov - 26 Nov

A modern interior with a geometric bookshelf filled with books, a bench, and a lamp.

19. Arlo Chicago

Theatre District, 12.5 km from Sleepy Hollow

Daniel

includes taxes & fees

26 Nov - 27 Nov

A rooftop terrace with outdoor seating, a pergola, and a view of surrounding high-rise buildings.

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

11.4 km from Sleepy Hollow

Danielle

includes taxes & fees

22 Nov - 23 Nov

View all properties

Compare popular hotels in Sleepy Hollow

Property	Property class	Guest rating
Carleton of Oak Park	3.0 star property	9.2 Wonderful 1,209 reviews	View
Sable at Navy Pier Chicago, Curio Collection by Hilton	4.0 star property	9.4 Exceptional 2,762 reviews	View
Hyatt House Chicago/West Loop-Fulton Market	3.5 star property	9.0 Wonderful 1,316 reviews	View
Hilton Garden Inn Chicago Downtown South Loop	3.0 star property	8.8 Excellent 2,203 reviews	View
Le Méridien Essex Chicago	4.0 star property	9.0 Wonderful 1,003 reviews	View

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas 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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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A large, historic building with a central tower and multiple windows, located near a body of water.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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Top Sleepy Hollow Hotel Reviews

Sports Illustrated Resorts Chicago

8/10 Good

"The hotel didn’t meet my expectations for the view, but it definitely had one of the best locations. The location was absolutely unbeatable, with easy walking access to Millennium Park, the Chicago Riverwalk, the Chicago Theatre, Art institute of Chicago and many other downtown attractions. It made exploring the city on foot incredibly convenient and enjoyable. The room was comfortable, and the overall atmosphere had a distinctive character. I especially appreciated being able to reach so many of Chicago’s highlights without having to rely on transportation. My only disappointment was the view, which fell short of what I had hoped for. However, the hotel’s prime location made up for much of that disappointment. Overall, it was a convenient and enjoyable place to stay for a few days in Chicago. I would recommend it to travelers who prioritize location and easy access to the city’s main attractions over a spectacular room view."

L7 Chicago by LOTTE

10/10 Excellent

"Have stayed at this hotel several times and always am very happy with staff and accommodations. It’s my favorite hotel in Chicago and I’ve stayed in many over the years. Maura (?) at front desk was helpful, professional and friendly. The cheerful concierge, Antonio, always is a pleasure and very helpful. Love the coffee in the lobby! Housekeeping does an exemplary job. Rooms here always are kept up, appearing newly furnished and extremely clean. I would prefer a larger fridge but rooms generally are nicely outfitted. I very much appreciate the attention to environmental issues, like bathroom cold water being filtered and drinkable. Location is great for me - not far from the Art Institute and a short taxi ride to the Lyric Opera. Sent from my iPhone"

Frequently asked questions

What's it like in Sleepy Hollow?

Sleepy Hollow is a neighbourhood that travellers 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 reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and be given a refund within 24 hours of your booking. Put your dates in and click on "Search", then filter by "fully refundable" to view the top deals on offer in Sleepy Hollow.

What can I see and do in this Chicago neighbourhood?

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.

Hotels in Sleepy Hollow

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Property class

Guest rating

Our top choices for Sleepy Hollow hotels

1. Carleton of Oak Park

2. Hyatt House Chicago/West Loop-Fulton Market

3. Best Western Grant Park Hotel

4. Hilton Garden Inn Chicago Downtown South Loop

5. Homewood Suites by Hilton Chicago Downtown South Loop

6. Le Méridien Essex Chicago

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

8. Level Chicago Fulton Market

9. Hyatt Place Chicago/Downtown - The Loop

10. Crowne Plaza Chicago West Loop by IHG

11. Congress Plaza Hotel

12. Cambria Hotel Chicago Loop - Theatre District

13. Hampton Inn & Suites Chicago Downtown

14. citizenM Chicago Downtown

15. Hilton Vacation Club Hotel Blake Chicago

16. Claridge House Chicago, Tapestry Collection by Hilton

17. La Quinta Inn & Suites by Wyndham Chicago Downtown

18. Hampton Inn Chicago West Loop Fulton Market Area

19. Arlo Chicago

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

Compare popular hotels in Sleepy Hollow

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Sports Illustrated Resorts Chicago

Frequently asked questions

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