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Check prices for these dates

This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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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

Carleton of Oak Park
3.0 star property
9.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,194 reviews)
"Definitely a boutique hotel, but we'll maintained and in a good area with good eateries close."
United States
Brad
The price is ฿4,091
฿4,540 total
includes taxes & fees
27 Oct - 28 Oct
Carleton of Oak Park
A rooftop lounge with a city view, featuring a sofa, tables, and a fire feature.

2. Hyatt House Chicago/West Loop-Fulton Market

Hyatt House Chicago/West Loop-Fulton Market
3.5 star property
10.6 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,309 reviews)
"Location was amazing. Loved the outdoor market in walking distance"
United States
Georgianna
The price is ฿6,518
฿7,749 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt House Chicago/West Loop-Fulton Market
A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

3. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
4.0 star property
The Loop, 11.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (1,221 reviews)
"Great location!"
United States
Mario
The price is ฿5,744
฿6,829 total
includes taxes & fees
3 Nov - 4 Nov
Hilton Vacation Club Hotel Blake Chicago
A modern living room with a blue sofa, a wooden coffee table, and a TV mounted on the wall displaying a welcome screen.

4. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.4 out of 10, Exceptional, (5,555 reviews)
"Excellent staff, excellent location, great resort style breakfast buffet"
United States
Scott E
The price is ฿6,187
฿8,308 total
includes taxes & fees
11 Nov - 12 Nov
Hotel Riu Plaza Chicago
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

5. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
The Loop, 12.7 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,881 reviews)
"It was a very nice stay! We enjoyed the hotel The views were amazing"
United States
James
The price is ฿7,330
฿9,709 total
includes taxes & fees
15 Nov - 16 Nov
LondonHouse Chicago, Curio Collection by Hilton
A modern kitchen with a large window, a dining area, and a view of the sea.

6. Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,528 reviews)
"Clean room great breakfast loved the pool"
United States
Cynthia
The price is ฿4,801
฿5,708 total
includes taxes & fees
10 Nov - 11 Nov
Homewood Suites by Hilton Chicago Downtown South Loop
A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

7. Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
River North, 12.9 km from Sleepy Hollow
8.6 out of 10, Excellent, (5,989 reviews)
"I’d stay here again."
United States
Eliana
The price is ฿4,978
฿6,785 total
includes taxes & fees
2 Nov - 3 Nov
Embassy Suites by Hilton Chicago Downtown River North
A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

8. Hyatt Place Chicago/River North

Hyatt Place Chicago/River North
3.5 star property
River North, 12.6 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,922 reviews)
"Great location!"
United States
Nilofar
The price is ฿5,816
฿6,914 total
includes taxes & fees
12 Nov - 13 Nov
Hyatt Place Chicago/River North
A multi-story hotel with a prominent sign reading "Crowne Plaza."

9. Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG
3.5 star property
10.9 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,741 reviews)
"Nice hotel and location was perfect."
United States
Chriselda
The price is ฿5,370
฿6,384 total
includes taxes & fees
1 Nov - 2 Nov
Crowne Plaza Chicago West Loop by IHG
A spacious bar area with high ceilings and large windows, offering views of a cityscape.

10. Hyatt Regency Chicago

Hyatt Regency Chicago
4.0 star property
The Loop, 12.9 km from Sleepy Hollow
9.4 out of 10, Exceptional, (3,519 reviews)
"The hotel was beautiful, great location"
United States
Addison
The price is ฿8,824
฿11,683 total
includes taxes & fees
31 Oct - 1 Nov
Hyatt Regency Chicago
A modern hotel with a glass facade, multiple floors, and a prominent sign.

11. Hampton Inn Chicago West Loop Fulton Market Area

Hampton Inn Chicago West Loop Fulton Market Area
2.5 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,009 reviews)
"Nice location, good breakfast Comfortable beds"
United States
Terri
The price is ฿7,099
฿8,440 total
includes taxes & fees
30 Oct - 31 Oct
Hampton Inn Chicago West Loop Fulton Market Area
The Intercontinental hotel facade with a large American flag and a floral display.

12. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
4.5 star property
Magnificent Mile, 13 km from Sleepy Hollow
9.2 out of 10, Wonderful, (3,397 reviews)
"Great hotel"
United States
Said Lopez
The price is ฿7,086
฿9,594 total
includes taxes & fees
31 Oct - 1 Nov
InterContinental Chicago Magnificent Mile by IHG
A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

13. Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown
3.0 star property
River North, 12.7 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,573 reviews)
"Great stay! Recommend for families who want to explore the city!"
United States
Erin
The price is ฿4,357
฿5,192 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Chicago Downtown
An indoor swimming pool with clear glass walls, a wooden ceiling, and a view of a red brick building.

14. Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
The Loop, 11.4 km from Sleepy Hollow
8.8 out of 10, Excellent, (2,197 reviews)
"Great place to stay at"
United States
Aran
The price is ฿4,091
฿4,864 total
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Chicago Downtown South Loop
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.

15. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Theatre District, 12.6 km from Sleepy Hollow
9.6 out of 10, Exceptional, (5,069 reviews)
"We really enjoyed our stay. The location is great and we enjoyed the amenities and our room."
United States
Amanda
The price is ฿5,604
฿6,663 total
includes taxes & fees
1 Nov - 2 Nov
L7 Chicago by LOTTE
A spacious lobby with a wooden floor, a central round table with decorative items, a reception desk, and framed artwork on the walls.

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

Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
3.0 star property
11.4 km from Sleepy Hollow
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice place"
United States
Brock
The price is ฿6,449
฿7,667 total
includes taxes & fees
30 Oct - 31 Oct
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
A modern restaurant interior with a green wall, hanging lights, and a long dining area.

17. Hotel 505 River North

Hotel 505 River North
4.5 star property
River North, 12.8 km from Sleepy Hollow
9.2 out of 10, Wonderful, (2,968 reviews)
"Ideal location, excellent large rooms."
United Kingdom
Jordan
The price is ฿5,728
฿7,880 total
includes taxes & fees
25 Oct - 26 Oct
Hotel 505 River North
A hotel room with a large window offering a city view, a bed, a desk, and a chair.

18. Courtyard by Marriott Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile
3.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (2,087 reviews)
"Great location Staff was terrific"
United States
Richard
The price is ฿4,574
฿5,438 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Chicago Magnificent Mile
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.

19. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Streeterville, 13.4 km from Sleepy Hollow
8.6 out of 10, Excellent, (3,337 reviews)
"nice chic clean place to stay near navy pier"
United States
Jonathan M
The price is ฿4,836
฿5,750 total
includes taxes & fees
1 Nov - 2 Nov
Aloft by Marriott Chicago Mag Mile
A spacious lobby with a checkered floor, a large sofa, and multiple chairs.

20. Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
3.0 star property
Streeterville, 13.3 km from Sleepy Hollow
9.0 out of 10, Wonderful, (1,006 reviews)
"Overall everything was great!"
United States
Annabella
The price is ฿4,731
฿5,625 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

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

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.

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.

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.

Top Sleepy Hollow Hotel Reviews

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"Cl"
Heaven 1-night trip
Posted less than an hour ago
The Chicago Hotel Collection - Magnificent Mile

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.