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

Sable at Navy Pier Chicago, Curio Collection by Hilton

Streeterville, 14.4 km from Sleepy Hollow

Deborah

₹28,927 total

includes taxes & fees

7 Jul - 8 Jul

Omni Chicago Hotel

Streeterville, 13.2 km from Sleepy Hollow

Bruce

₹17,670 total

includes taxes & fees

1 Jul - 2 Jul

Congress Plaza Hotel

The Loop, 11.9 km from Sleepy Hollow

Felipa

₹15,374 total

includes taxes & fees

29 Jun - 30 Jun

Palmer House a Hilton Hotel

Theatre District, 12.1 km from Sleepy Hollow

Charles Otto

₹26,558 total

includes taxes & fees

9 Jul - 10 Jul

Hotel Riu Plaza Chicago

Streeterville, 13.3 km from Sleepy Hollow

Corey

₹20,795 total

includes taxes & fees

6 Jul - 7 Jul

Travelodge by Wyndham Downtown Chicago

The Loop, 11.8 km from Sleepy Hollow

Ming

₹15,283 total

includes taxes & fees

1 Jul - 2 Jul

Staypineapple, An Iconic Hotel, The Loop

Theatre District, 12.2 km from Sleepy Hollow

Debby

₹18,539 total

includes taxes & fees

6 Jul - 7 Jul

Swissotel - Chicago

13 km from Sleepy Hollow

Martha

₹23,252 total

includes taxes & fees

1 Jul - 2 Jul

Silversmith Hotel Chicago Downtown

Theatre District, 12.2 km from Sleepy Hollow

Gabino

₹17,709 total

includes taxes & fees

6 Jul - 7 Jul

The Blackstone, Autograph Collection

The Loop, 11.8 km from Sleepy Hollow

Neydee

₹20,345 total

includes taxes & fees

6 Jul - 7 Jul

2 restaurants; breakfast, lunch and dinner served

LondonHouse Chicago, Curio Collection by Hilton

The Loop, 12.7 km from Sleepy Hollow

Robert

₹26,709 total

includes taxes & fees

1 Jul - 2 Jul

Eurostars Magnificent Mile

River North, 13 km from Sleepy Hollow

Audrey

₹16,283 total

includes taxes & fees

2 Jul - 3 Jul

Best Western Grant Park Hotel

The Loop, 11.5 km from Sleepy Hollow

Alexandra

₹13,479 total

includes taxes & fees

1 Jul - 2 Jul

Hilton Chicago/Magnificent Mile Suites

Streeterville, 13.8 km from Sleepy Hollow

Avradita

₹18,082 total

includes taxes & fees

30 Jun - 1 Jul

The Chicago Hotel Collection Ambassador Gold Coast

Gold Coast, 13.9 km from Sleepy Hollow

Zhiwen

₹17,675 total

includes taxes & fees

1 Jul - 2 Jul

Sheraton Grand Chicago Riverwalk

Streeterville, 13.2 km from Sleepy Hollow

Pamela

₹29,751 total

includes taxes & fees

8 Jul - 9 Jul

Hyatt Regency Chicago

The Loop, 12.9 km from Sleepy Hollow

Marianne

₹27,727 total

includes taxes & fees

9 Jul - 10 Jul

Hilton Garden Inn Chicago Downtown South Loop

The Loop, 11.4 km from Sleepy Hollow

Justin

₹17,525 total

includes taxes & fees

2 Jul - 3 Jul

Presidential Suite, 1 Bedroom, Non Smoking | Premium bedding, in-room safe, desk, blackout curtains

Hotel 55 Chicago Downtown

River North, 13.1 km from Sleepy Hollow

Matt

₹18,772 total

includes taxes & fees

2 Jul - 3 Jul

Fairmont Chicago at Millennium Park

The Loop, 12.9 km from Sleepy Hollow

Mohammed Izzal

₹26,291 total

includes taxes & fees

6 Jul - 7 Jul

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Where to stay in Sleepy Hollow

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

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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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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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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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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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

Travelodge by Wyndham Downtown Chicago

10/10 Excellent

"Easy access to everything"

Crowne Plaza Chicago West Loop by IHG

6/10 Okay

"Received a message from the hotel in advance that, among other details, parking is available in the garage across the courtyard. Arrived, pulled into garage and into a hotel designated spot in the garage. But at check-in was told all hotel spots were reserved, no more were available, and I needed to move my vehicle. There was no such detail in the advance information -- and it seems pretty important. Also, there was no way to lock/secure the bathroom door."

Freehand Chicago

6/10 Okay

"I haven't stayed at a hotel/hostel before, so I don't know if my expectations were unreasonable. First, the good. The staff were friendly and helpful. The location was perfect. The hot water and AC were plentiful. I felt safe and wasn't bothered by noise from neighbors. I didn't see any bugs. They even had a live musician during at least one of the evenings I was there. Now the bad. We had a private quad. It was dirty. The walls, some of the bedding, the bunk bed curtains were stained and gross. We found trash from the previous guests. There was so much dust and debris, especially in the part of the bunks that held the mattresses. The shower curtain and tiles were moldy. The room needed a good scrubbing and a fresh coat of paint. I wouldn't stay there again unless they improved their housekeeping."

Search Hotels in Sleepy Hollow, Chicago

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Our top choices for Sleepy Hollow hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Omni Chicago Hotel

Congress Plaza Hotel

Palmer House a Hilton Hotel

Hotel Riu Plaza Chicago

Travelodge by Wyndham Downtown Chicago

Staypineapple, An Iconic Hotel, The Loop

Swissotel - Chicago

Silversmith Hotel Chicago Downtown

The Blackstone, Autograph Collection

LondonHouse Chicago, Curio Collection by Hilton

Eurostars Magnificent Mile

Best Western Grant Park Hotel

Hilton Chicago/Magnificent Mile Suites

The Chicago Hotel Collection Ambassador Gold Coast

Sheraton Grand Chicago Riverwalk

Hyatt Regency Chicago

Hilton Garden Inn Chicago Downtown South Loop

Hotel 55 Chicago Downtown

Fairmont Chicago at Millennium Park

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Travelodge by Wyndham Downtown Chicago

Frequently asked questions

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