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.

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

₹12,921 total

includes taxes & fees

5 Nov - 6 Nov

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

2. Hilton Vacation Club Hotel Blake Chicago

The Loop, 11.6 km from Sleepy Hollow

tahira

₹18,127 total

includes taxes & fees

22 Nov - 23 Nov

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

3. LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.7 km from Sleepy Hollow

James

₹19,074 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.

4. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

JESUS VERA

₹17,151 total

includes taxes & fees

23 Nov - 24 Nov

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

5. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Georgianna

₹16,285 total

includes taxes & fees

22 Nov - 23 Nov

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

6. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Pamela

₹13,457 total

includes taxes & fees

22 Nov - 23 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.

7. L7 Chicago by LOTTE

Theatre District, 12.6 km from Sleepy Hollow

Matthew

₹16,396 total

includes taxes & fees

22 Nov - 23 Nov

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

8. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Eliana

₹14,322 total

includes taxes & fees

23 Nov - 24 Nov

A modern lobby with a seating area, a bar, and a large screen wall.

9. Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Addison

₹23,183 total

includes taxes & fees

23 Nov - 24 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

Miya

₹15,631 total

includes taxes & fees

22 Nov - 23 Nov

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

11. Swissotel - Chicago

13 km from Sleepy Hollow

Oleg

₹16,543 total

includes taxes & fees

26 Nov - 27 Nov

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

12. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Richard

₹12,960 total

includes taxes & fees

23 Nov - 24 Nov

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

13. Fairmont Chicago at Millennium Park

The Loop, 12.9 km from Sleepy Hollow

Ruby

₹25,899 total

includes taxes & fees

23 Nov - 24 Nov

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

14. The Royal Sonesta Chicago Downtown

The Loop, 12.7 km from Sleepy Hollow

Scott

₹17,632 total

includes taxes & fees

26 Nov - 27 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.

15. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Jena

₹12,380 total

includes taxes & fees

22 Nov - 23 Nov

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

16. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 13 km from Sleepy Hollow

Nellie

₹24,608 total

includes taxes & fees

25 Nov - 26 Nov

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

17. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

Cordula

₹13,354 total

includes taxes & fees

24 Nov - 25 Nov

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

18. Eurostars Magnificent Mile

River North, 13 km from Sleepy Hollow

Gabriela

₹17,099 total

includes taxes & fees

22 Nov - 23 Nov

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

19. citizenM Chicago Downtown

Theatre District, 12.7 km from Sleepy Hollow

Katarina

₹13,118 total

includes taxes & fees

23 Nov - 24 Nov

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

20. Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Melissa

₹13,361 total

includes taxes & fees

23 Nov - 24 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.

See properties

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.

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

Congress Plaza Hotel

10/10 Excellent

"."

Sports Illustrated Resorts Chicago

8/10 Good

"Solid hotel in a great location. We were there as they were transferring to a full launch of the SI branded hotel. Good gym, rooms are well appointed. During our visit they had an all inclusive rooftop bar from 3-7pm every day which was a great touch but nobody actually told us about it, we kind of found it ourselves. Good option for a hotel in downtown Chicago though!"

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"

Search Hotels in Sleepy Hollow, Chicago

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Sleepy Hollow hotels

1. Carleton of Oak Park

2. Hilton Vacation Club Hotel Blake Chicago

3. LondonHouse Chicago, Curio Collection by Hilton

4. Hotel Riu Plaza Chicago

5. Hyatt House Chicago/West Loop-Fulton Market

6. Hyatt Place Chicago/River North

7. L7 Chicago by LOTTE

8. Embassy Suites by Hilton Chicago Downtown River North

9. Hyatt Regency Chicago

10. Hotel 505 River North

11. Swissotel - Chicago

12. Courtyard by Marriott Chicago Magnificent Mile

13. Fairmont Chicago at Millennium Park

14. The Royal Sonesta Chicago Downtown

15. Aloft by Marriott Chicago Mag Mile

16. InterContinental Chicago Magnificent Mile by IHG

17. Hyatt Place Chicago/Downtown - The Loop

18. Eurostars Magnificent Mile

19. citizenM Chicago Downtown

20. Hilton Chicago/Magnificent Mile Suites

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

Congress Plaza Hotel

Frequently asked questions

Explore a world of travel with Expedia