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

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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

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

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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

Hilton Chicago/Magnificent Mile Suites

8/10 Good

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Aloft by Marriott Chicago Mag Mile

6/10 Okay

"Room was okay but dated and needed some repairs/TLC. King bedding was ill fitted. Bathroom “barn door” needed some greasing. Was in a handicap-able room, the shower curtain could have been lower to limit was leaking outside shower stall. Staff was helpful but looked annoyed most of the time. They did help explain deposit charge process & helped me with a package drop off while staying. Lobby market food was overpriced and underwhelming. No breakfast provided but coffee/tea offering was okay until to get you started for the day. Housekeeping was amazing and super efficient."

Fairmont Chicago at Millennium Park

8/10 Good

"Stayed here for a recent trip to Chicago and overall the experience was okay. The location is convenient for downtown attractions and Millennium Park, and the hotel itself was clean and comfortable. Staff were generally polite and check-in was fairly smooth. The rooms were decent, though some areas felt a little dated for the price. Amenities and service were fine but nothing especially memorable. It worked well as a place to stay while exploring the city, but I expected a bit more considering the reputation and cost. Good option if location is your priority, but not necessarily a standout luxury experience."

The Chicago Hotel Collection Ambassador Gold Coast

2/10 Terrible

"Terrible hotel, when I made the reservation they told me I had free breakfast but they charged me $70 extra for it, very dirty carpet, loud AC, no water in the room even though I was trying to pay so I had to go down lobby at 3am to get water, over all one of the horrible hotel I stayed 👎👎"

Hotel Riu Plaza Chicago

10/10 Excellent

"This is an amazing hotel at this price. The complimentary buffet breakfast each morning is unbelievable. That alone is great, add to that great service. Gerardo at the front desk was great, got us checked in right away and always made sure to ask if there was anything we needed. The room was modern and clean. Great bathroom and very comfortable bed. I would recommend this hotel to anyone looking for a great hotel in downtown Chicago. Almost forgot to mention the perfect location!"

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent

"The hotel is in an excellent location, close to everything, which made the stay very convenient and enjoyable. The rooms were very clean, spacious, and comfortable, and the entire hotel felt well maintained and beautiful. The staff was also very friendly and welcoming throughout the stay, which made the experience even better. The only thing I would suggest improving is the breakfast variety. While the breakfast was good, I feel it could offer a few more options to better match the overall level and quality of the hotel. Overall, I would definitely recommend this hotel because of its cleanliness, comfort, great service, and one of the best locations in Chicago."

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?

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

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Our top choices for Sleepy Hollow hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

The Wade

Sheraton Grand Chicago Riverwalk

Swissotel - Chicago

DoubleTree by Hilton Chicago - Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Radisson Blu Aqua Hotel Chicago

Fairmont Chicago at Millennium Park

Aloft by Marriott Chicago Mag Mile

Ivy Boutique Hotel

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Millennium Hotel Knickerbocker Chicago

Hyatt Regency Chicago

Hyatt Centric Chicago Magnificent Mile

Courtyard by Marriott Chicago Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

Hotel Riu Plaza Chicago

Congress Plaza Hotel

Where to stay in Sleepy Hollow

Downtown Chicago

Magnificent Mile

The Loop

River North

Lincoln Park

Top Sleepy Hollow Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

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