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 Works Museum and Jedlica Performing Arts Center are just a few of the places to visit in and around Sleepy Hollow. When you're sightseeing in Chicago, Los Globos and Balzekas Museum of Lithuanian Culture are also worth a stop.

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

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Our top choices for Sleepy Hollow hotels

1. Hyatt House Chicago/West Loop-Fulton Market

10.6 km from Sleepy Hollow

Hadi

₹26,107 total

includes taxes & fees

9 Aug - 10 Aug

2. Hyatt Place Chicago/Downtown - The Loop

The Loop, 11.7 km from Sleepy Hollow

Kimberly

₹26,062 total

includes taxes & fees

23 Aug - 24 Aug

3. La Quinta Inn & Suites by Wyndham Chicago Downtown

The Loop, 11.6 km from Sleepy Hollow

Diana

₹22,128 total

includes taxes & fees

9 Aug - 10 Aug

4. Crowne Plaza Chicago West Loop by IHG

10.9 km from Sleepy Hollow

Navin

₹20,110 total

includes taxes & fees

20 Aug - 21 Aug

5. Hilton Garden Inn Chicago Central Loop

The Loop, 11.4 km from Sleepy Hollow

Dawn

₹24,130 total

includes taxes & fees

9 Aug - 10 Aug

6. Aloft by Marriott Chicago Mag Mile

Streeterville, 13.4 km from Sleepy Hollow

Donna

₹21,319 total

includes taxes & fees

9 Aug - 10 Aug

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

Streeterville, 14.4 km from Sleepy Hollow

Morgan

₹29,664 total

includes taxes & fees

9 Aug - 10 Aug

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

11.4 km from Sleepy Hollow

Jihi

₹24,226 total

includes taxes & fees

9 Aug - 10 Aug

9. Hampton Inn Chicago West Loop Fulton Market Area

11.4 km from Sleepy Hollow

Michele

₹26,082 total

includes taxes & fees

16 Aug - 17 Aug

10. Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Deanne

₹27,226 total

includes taxes & fees

23 Aug - 24 Aug

11. InterContinental Chicago Magnificent Mile by IHG

Magnificent Mile, 13 km from Sleepy Hollow

Jose

₹32,084 total

includes taxes & fees

17 Aug - 18 Aug

12. Hyatt Place Chicago/River North

River North, 12.6 km from Sleepy Hollow

Michelle

₹19,381 total

includes taxes & fees

9 Aug - 10 Aug

13. Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Emily

₹33,517 total

includes taxes & fees

9 Aug - 10 Aug

14. Hilton Chicago

The Loop, 11.7 km from Sleepy Hollow

kun

₹33,726 total

includes taxes & fees

23 Aug - 24 Aug

Premium bedding, in-room safe, desk, blackout curtains

15. Courtyard by Marriott Chicago Magnificent Mile

Streeterville, 13.3 km from Sleepy Hollow

Zachary

₹24,511 total

includes taxes & fees

16 Aug - 17 Aug

16. Embassy Suites by Hilton Chicago Downtown River North

River North, 12.9 km from Sleepy Hollow

Erin

₹22,969 total

includes taxes & fees

16 Aug - 17 Aug

17. Hilton Garden Inn Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Heather

₹21,389 total

includes taxes & fees

10 Aug - 11 Aug

Suite, 1 Bedroom, Corner | Private kitchen | Coffee/tea maker, full-sized fridge, microwave, stovetop

18. Homewood Suites by Hilton Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

jayne

₹21,326 total

includes taxes & fees

19 Aug - 20 Aug

19. Hampton Inn Majestic Chicago Theatre District

Theatre District, 12 km from Sleepy Hollow

Naidy

₹21,408 total

includes taxes & fees

9 Aug - 10 Aug

20. Hyatt Centric The Loop Chicago

Theatre District, 11.8 km from Sleepy Hollow

Dee

₹24,629 total

includes taxes & fees

16 Aug - 17 Aug

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Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.

A busy city street with tall buildings, a bus, and cars.

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 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 historic castle-like building with intricate stonework and a paved walkway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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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.

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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

River Hotel

10/10 Excellent

"Everything good and perfet"

Congress Plaza Hotel

8/10 Good

"Staff was helpful especially because I kept locking myself out of my room. It's a bit older hotel so it was a little unclear how to turn off or lower the air because I kept looking for a digital thermostat, buts it's a knob hidden under a little door on the air itself. Bed was comfortable. The room itself has been mostly modernized, but the bath tub was kinda old and had some suspicious brown stains and a bandage shaped thing by the drain that looked painted over. I could not removed either of these with a wet towel. Took a little while for the water to get hot, but when it did, it was hot. There was a lot of street noise from noisy loud motors, sirens, and loud music. My room was connected to another room unfortunately, so I could hear my neighbors's music/TV and every time their FB messenger went off. Wifi didn't really work. Nice location though. Close to public transport and walking distance to the parks and other things I went to."

Warwick Allerton - Chicago

8/10 Good

"We had a great stay for one night. The location is excellent, right on the main shopping street and within easy walking distance of lots of shops and attractions. The hotel offers reasonably priced luggage storage, which was really convenient, and we were able to check in early for an additional fee, which was worth it after travelling. There’s also a good café in the hotel, perfect for grabbing breakfast or a coffee. The room was a little small and slightly dated, but it was clean, comfortable, and perfectly adequate for what we needed for a one-night stay. Overall, we’d definitely stay here again for the location and convenience."

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"Nice pool and fitness center. The room was basic two double beds but outlets only available between the beds. This does not work well when two people want to charge their phones. Luggage can be checked for the day after checkout at the bell desk, but the process was inefficient and slow. Only 4 elevators for 26 floors. Parking across the street at Nordstrom's (enter on Rush) was convenient, booked through Spothero, and saved $40 over valet parking. All in all, you are paying for the location."

Search Hotels in Sleepy Hollow, Chicago

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Our top choices for Sleepy Hollow hotels

1. Hyatt House Chicago/West Loop-Fulton Market

2. Hyatt Place Chicago/Downtown - The Loop

3. La Quinta Inn & Suites by Wyndham Chicago Downtown

4. Crowne Plaza Chicago West Loop by IHG

5. Hilton Garden Inn Chicago Central Loop

6. Aloft by Marriott Chicago Mag Mile

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

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

9. Hampton Inn Chicago West Loop Fulton Market Area

10. Hotel Riu Plaza Chicago

11. InterContinental Chicago Magnificent Mile by IHG

12. Hyatt Place Chicago/River North

13. Hyatt Regency Chicago

14. Hilton Chicago

15. Courtyard by Marriott Chicago Magnificent Mile

16. Embassy Suites by Hilton Chicago Downtown River North

17. Hilton Garden Inn Chicago Downtown South Loop

18. Homewood Suites by Hilton Chicago Downtown South Loop

19. Hampton Inn Majestic Chicago Theatre District

20. Hyatt Centric The Loop Chicago

Where to stay in Sleepy Hollow

Downtown Chicago

The Loop

Magnificent Mile

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

River Hotel

Frequently asked questions

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