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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

Rp2.431.400 total

includes taxes & fees

1 Nov - 2 Nov

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

2. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.7 km from Sleepy Hollow

Keeven

Rp5.402.238 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.

3. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

Mario

Rp3.656.773 total

includes taxes & fees

3 Nov - 4 Nov

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

4. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Kevin

Rp4.250.517 total

includes taxes & fees

11 Nov - 12 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.

5. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Jeffrey Thomas

Rp4.140.091 total

includes taxes & fees

1 Nov - 2 Nov

A room with two chairs and a small table, a large window with a city view at night.

6. Eurostars Magnificent Mile

River North, 13 km from Sleepy Hollow

Will

Rp3.254.146 total

includes taxes & fees

1 Nov - 2 Nov

A dining area with a table set for four, large windows offering a cityscape view at dusk.

7. The Royal Sonesta Chicago Downtown

The Loop, 12.7 km from Sleepy Hollow

Jordyn

Rp4.917.757 total

includes taxes & fees

11 Nov - 12 Nov

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

8. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 13 km from Sleepy Hollow

Reginald

Rp5.141.870 total

includes taxes & fees

31 Oct - 1 Nov

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

9. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Iminique

Rp3.620.452 total

includes taxes & fees

1 Nov - 2 Nov

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

10. Hotel 505 River North

River North, 12.8 km from Sleepy Hollow

Giana

Rp4.598.544 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a marble island, fruit bowls, and a city view.

11. Fairmont Chicago at Millennium Park

The Loop, 12.9 km from Sleepy Hollow

Ruby

Rp6.051.317 total

includes taxes & fees

4 Nov - 5 Nov

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

12. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Eliana

Rp3.602.348 total

includes taxes & fees

1 Nov - 2 Nov

A dining table set for six with a cityscape view through large windows.

13. Swissotel - Chicago

13 km from Sleepy Hollow

Rp6.285.189 total

includes taxes & fees

25 Oct - 26 Oct

An outdoor seating area with modern furniture and potted plants.

14. Radisson Blu Aqua Hotel Chicago

12.9 km from Sleepy Hollow

Shannon

Rp5.595.060 total

includes taxes & fees

31 Oct - 1 Nov

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

15. Hampton Inn Chicago-O'Hare International Airport

19.4 km from Sleepy Hollow

Jennifer

Rp2.574.546 total

includes taxes & fees

1 Nov - 2 Nov

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

16. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Rp4.152.870 total

includes taxes & fees

1 Nov - 2 Nov

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

17. citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

Katarina

Rp3.620.451 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with a reception desk, marble flooring, and elegant chandeliers.

18. Silversmith Hotel Chicago Downtown

Theatre District, 12.2 km from Sleepy Hollow

Guy

Rp3.625.898 total

includes taxes & fees

1 Nov - 2 Nov

A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.

19. The Wade

Streeterville, 13.8 km from Sleepy Hollow

Erin

Rp2.704.690 total

includes taxes & fees

12 Nov - 13 Nov

A modern rooftop lounge with white seating, a glass ceiling, and city views.

20. The Godfrey Hotel Chicago

River North, 12.8 km from Sleepy Hollow

Rp3.790.166 total

includes taxes & fees

2 Nov - 3 Nov

View all properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Top Sleepy Hollow Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Busy hotel but very clean, walkable to a lot of things, rooftop was nice but not many people up there at the time of my visit. Enjoyed the spacious rooms, free water, gym, bar, and everything else."

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.

Explore a world of travel with Expedia

Book Hotels in Sleepy Hollow on Expedia.com

Search Hotels in Sleepy Hollow, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sleepy Hollow hotels

1. Carleton of Oak Park

2. LondonHouse Chicago, Curio Collection by Hilton

3. Hilton Vacation Club Hotel Blake Chicago

4. Hotel Riu Plaza Chicago

5. L7 Chicago by LOTTE

6. Eurostars Magnificent Mile

7. The Royal Sonesta Chicago Downtown

8. InterContinental Chicago Magnificent Mile by IHG

9. Hyatt Place Chicago/River North

10. Hotel 505 River North

11. Fairmont Chicago at Millennium Park

12. Embassy Suites by Hilton Chicago Downtown River North

13. Swissotel - Chicago

14. Radisson Blu Aqua Hotel Chicago

15. Hampton Inn Chicago-O'Hare International Airport

16. Hyatt House Chicago/West Loop-Fulton Market

17. citizenM Chicago Downtown

18. Silversmith Hotel Chicago Downtown

19. The Wade

20. The Godfrey Hotel Chicago

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 - Magnificent Mile

Frequently asked questions

Explore a world of travel with Expedia