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

RM555 total

includes taxes & fees

3 Nov - 4 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

RM671 total

includes taxes & fees

23 Nov - 24 Nov

A modern interior with a bar area, seating, and decorative wooden panels.

3. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Michelle

RM477 total

includes taxes & fees

23 Nov - 24 Nov

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

4. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Nicole

RM512 total

includes taxes & fees

23 Nov - 24 Nov

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

5. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

tahira

RM779 total

includes taxes & fees

22 Nov - 23 Nov

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

6. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

Cordula

RM573 total

includes taxes & fees

23 Nov - 24 Nov

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

7. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Chriselda

RM651 total

includes taxes & fees

25 Nov - 26 Nov

An outdoor dining area with tables and umbrellas, overlooking a river with a bridge and high-rise buildings in the background.

8. Holiday Inn Chicago Dwtn - The Mart by IHG

River North, 11.9 km from Sleepy Hollow

Pamela

RM778 total

includes taxes & fees

22 Nov - 23 Nov

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

9. Hampton Inn Chicago West Loop Fulton Market Area

11.4 km from Sleepy Hollow

Peggy.

RM710 total

includes taxes & fees

23 Nov - 24 Nov

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

10. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Aran

RM471 total

includes taxes & fees

23 Nov - 24 Nov

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

11. Hampton Inn & Suites Chicago Downtown

River North, 12.7 km from Sleepy Hollow

Tracy

RM514 total

includes taxes & fees

24 Nov - 25 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

12. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Matthew

RM705 total

includes taxes & fees

22 Nov - 23 Nov

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

13. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

JESUS VERA

RM737 total

includes taxes & fees

23 Nov - 24 Nov

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

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

11.4 km from Sleepy Hollow

Danielle

RM657 total

includes taxes & fees

22 Nov - 23 Nov

15. Hyatt Centric The Loop Chicago

Theatre District, 11.8 km from Sleepy Hollow

David

RM905 total

includes taxes & fees

1 Nov - 2 Nov

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

16. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Pamela

RM578 total

includes taxes & fees

22 Nov - 23 Nov

An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.

17. The Emily Hotel

11.1 km from Sleepy Hollow

Nico

RM933 total

includes taxes & fees

22 Nov - 23 Nov

A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

18. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Jena

RM532 total

includes taxes & fees

22 Nov - 23 Nov

A multi-story building with a prominent entrance featuring a large archway and a sign.

19. Hilton Chicago

The Loop, 11.7 km from Sleepy Hollow

Joanna

RM645 total

includes taxes & fees

27 Nov - 28 Nov

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

20. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Richard

RM557 total

includes taxes & fees

24 Nov - 25 Nov

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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 2,761 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, Chicago

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. Homewood Suites by Hilton Chicago Downtown South Loop

5. Hilton Vacation Club Hotel Blake Chicago

6. Hyatt Place Chicago/Downtown - The Loop

7. Crowne Plaza Chicago West Loop by IHG

8. Holiday Inn Chicago Dwtn - The Mart by IHG

9. Hampton Inn Chicago West Loop Fulton Market Area

10. Hilton Garden Inn Chicago Downtown South Loop

11. Hampton Inn & Suites Chicago Downtown

12. L7 Chicago by LOTTE

13. Hotel Riu Plaza Chicago

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

15. Hyatt Centric The Loop Chicago

16. Hyatt Place Chicago/River North

17. The Emily Hotel

18. Aloft by Marriott Chicago Mag Mile

19. Hilton Chicago

20. Courtyard by Marriott Chicago Magnificent Mile

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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