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

Next weekend

In two weeks

Our top choices for Sleepy Hollow hotels

1. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

LISA

6.779.583 ₫ total

includes taxes & fees

20 Sept - 21 Sept

2. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Phillip

5.055.709 ₫ total

includes taxes & fees

20 Sept - 21 Sept

3. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Valerie

8.068.835 ₫ total

includes taxes & fees

20 Sept - 21 Sept

Suite, 1 Bedroom, Corner | Private kitchen

4. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

AMBER

7.439.050 ₫ total

includes taxes & fees

27 Sept - 28 Sept

5. Hyatt Centric The Loop Chicago

Theatre District, 11.8 km from Sleepy Hollow

Tamika

8.322.134 ₫ total

includes taxes & fees

20 Sept - 21 Sept

6. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

Ann

9.733.019 ₫ total

includes taxes & fees

20 Sept - 21 Sept

7. DoubleTree by Hilton Chicago - Magnificent Mile

Streeterville, 13.4 km from Sleepy Hollow

Madelyn

5.631.676 ₫ total

includes taxes & fees

27 Sept - 28 Sept

8. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.6 km from Sleepy Hollow

Mythli

6.522.175 ₫ total

includes taxes & fees

20 Sept - 21 Sept

9. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Joel

8.628.561 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

Streeterville, 14.4 km from Sleepy Hollow

Shanequa

9.668.660 ₫ total

includes taxes & fees

27 Sept - 28 Sept

11. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Eric

6.810.399 ₫ total

includes taxes & fees

27 Sept - 28 Sept

12. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

christina

7.962.621 ₫ total

includes taxes & fees

1 Oct - 2 Oct

13. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Kristeen

5.998.388 ₫ total

includes taxes & fees

20 Sept - 21 Sept

14. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Jarred

8.315.074 ₫ total

includes taxes & fees

13 Oct - 14 Oct

15. Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Melissa

5.519.506 ₫ total

includes taxes & fees

29 Sept - 30 Sept

16. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Brian

6.260.330 ₫ total

includes taxes & fees

20 Sept - 21 Sept

17. citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

Isayra

5.947.544 ₫ total

includes taxes & fees

20 Sept - 21 Sept

18. Holiday Inn & Suites Chicago - Downtown by IHG

West Loop, 10.8 km from Sleepy Hollow

Jennifer

6.042.870 ₫ total

includes taxes & fees

20 Sept - 21 Sept

19. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Jacqueline

5.859.407 ₫ total

includes taxes & fees

20 Sept - 21 Sept

20. River Hotel

The Loop, 12.7 km from Sleepy Hollow

steve

4.688.697 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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.

See properties

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

See properties

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

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

See properties

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

See properties

Top Sleepy Hollow Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

8/10 Good

"Y"

Hampton Inn Chicago Downtown/Magnificent Mile

8/10 Good

"Our room was clean and always cool after being out all day on a sunny Labor Day weekend. The hotel had a room available for us to check in early. We took advantage of breakfast each morning and despite the fact that others complained about nowhere to sit for breakfast, we did not find that to be the case. Loved the location as we were close to many things. The elevators also seemed to be relatively available to us when we were leaving and coming back."

Warwick Allerton - Chicago

8/10 Good

"Property was very clean and enjoyed we enjoyed our room. However, there are a couple of down sides to mention. Upon arrival front desk staff was not very friendly when trying to find out where to store our bags before check in. Having to pay $2 per bag stored seemed unnecessary given the price we paid for the entirety of our stay. Additionally, when we went to retrieve our stored bags nobody was at the counter and the wait seemed unwarranted as there was a manger downstairs that could have helped but instead chose to tell us someone should be back soon. For the premium price we paid it definitely should have been better from a customer service viewpoint."

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. Hyatt Place Chicago/Downtown - The Loop

2. Crowne Plaza Chicago West Loop by IHG

3. Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4. Homewood Suites by Hilton Chicago Downtown South Loop

5. Hyatt Centric The Loop Chicago

6. Hilton Vacation Club Hotel Blake Chicago

7. DoubleTree by Hilton Chicago - Magnificent Mile

8. La Quinta Inn & Suites by Wyndham Chicago Downtown

9. Hyatt House Chicago/West Loop-Fulton Market

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

11. Hyatt Place Chicago/River North

12. L7 Chicago by LOTTE

13. Embassy Suites by Hilton Chicago Downtown River North

14. Hotel Riu Plaza Chicago

15. Best Western Grant Park Hotel

16. Hilton Chicago/Magnificent Mile Suites

17. citizenM Chicago Downtown

18. Holiday Inn & Suites Chicago - Downtown by IHG

19. Aloft by Marriott Chicago Mag Mile

20. River Hotel

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

Frequently asked questions

Explore a world of travel with Expedia