The Best Hotels in Sleepy Hollow, Chicago - 2026 Updated Prices

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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

฿4,555 total

includes taxes & fees

4 Nov - 5 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

฿7,797 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

3. Hampton Inn Chicago-O'Hare International Airport

19.4 km from Sleepy Hollow

Jennifer

฿4,834 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a large bed, a nightstand with a lamp, a wall clock, and a window with curtains.

4. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

Mario

฿6,871 total

includes taxes & fees

3 Nov - 4 Nov

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

5. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Iminique

฿6,797 total

includes taxes & fees

1 Nov - 2 Nov

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

6. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Kevin

฿7,956 total

includes taxes & fees

11 Nov - 12 Nov

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

7. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Eliana

฿6,763 total

includes taxes & fees

1 Nov - 2 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.

8. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Jeffrey Thomas

฿7,773 total

includes taxes & fees

1 Nov - 2 Nov

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

9. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Corinn

฿5,726 total

includes taxes & fees

10 Nov - 11 Nov

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

10. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.7 km from Sleepy Hollow

Keeven

฿10,177 total

includes taxes & fees

1 Nov - 2 Nov

The Intercontinental hotel facade with a large American flag and a floral display.

11. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 13 km from Sleepy Hollow

Reginald

฿9,625 total

includes taxes & fees

31 Oct - 1 Nov

An outdoor seating area with modern furniture and potted plants.

12. Radisson Blu Aqua Hotel Chicago

12.9 km from Sleepy Hollow

Shannon

฿10,505 total

includes taxes & fees

31 Oct - 1 Nov

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

13. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Shelby Ryann

฿5,003 total

includes taxes & fees

9 Nov - 10 Nov

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.

14. Hilton Chicago

The Loop, 11.7 km from Sleepy Hollow

Anna

฿7,592 total

includes taxes & fees

30 Oct - 31 Oct

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

15. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

Cordula

฿7,797 total

includes taxes & fees

1 Nov - 2 Nov

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

16. The Emily Hotel

11.1 km from Sleepy Hollow

Lori

฿9,287 total

includes taxes & fees

1 Nov - 2 Nov

A hotel lobby with a bar area, a chandelier, and a reception desk.

17. Residence Inn Chicago Downtown/Loop

Theatre District, 11.8 km from Sleepy Hollow

Karla

฿9,556 total

includes taxes & fees

30 Oct - 31 Oct

A hotel room with a sofa, a small table, and a view of the cityscape through large windows.

18. Fairfield Inn & Suites Chicago Downtown/River North

River North, 12.6 km from Sleepy Hollow

Cindy

฿6,598 total

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.

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

11.4 km from Sleepy Hollow

Brock

฿9,211 total

includes taxes & fees

30 Oct - 31 Oct

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

20. Hampton Inn & Suites Chicago Downtown

River North, 12.7 km from Sleepy Hollow

Catherine

฿5,574 total

includes taxes & fees

1 Nov - 2 Nov

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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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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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

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Great location, beautiful lobby area, quiet clean rooms."

The Godfrey Hotel Chicago

8/10 Good

"The hotel was nice, and the location was great. However, the property could use a little updating and more attention to detail, especially with the bathroom amenities. The hallways were also quite noisy, with a lot of partying going on. I certainly don’t mind people having a good time, but it did get a bit loud. Overall, it was an okay stay, but I felt it was overpriced for what was offered. There were other hotels nearby at about the same price that appeared to be substantially nicer. Not a bad experience, just not quite worth the price."

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.

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Our top choices for Sleepy Hollow hotels

1. Carleton of Oak Park

2. Hyatt House Chicago/West Loop-Fulton Market

3. Hampton Inn Chicago-O'Hare International Airport

4. Hilton Vacation Club Hotel Blake Chicago

5. Hyatt Place Chicago/River North

6. Hotel Riu Plaza Chicago

7. Embassy Suites by Hilton Chicago Downtown River North

8. L7 Chicago by LOTTE

9. Homewood Suites by Hilton Chicago Downtown South Loop

10. LondonHouse Chicago, Curio Collection by Hilton

11. InterContinental Chicago Magnificent Mile by IHG

12. Radisson Blu Aqua Hotel Chicago

13. Best Western Grant Park Hotel

14. Hilton Chicago

15. Hyatt Place Chicago/Downtown - The Loop

16. The Emily Hotel

17. Residence Inn Chicago Downtown/Loop

18. Fairfield Inn & Suites Chicago Downtown/River North

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

20. Hampton Inn & Suites Chicago Downtown

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

Frequently asked questions

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