Top 10 Sleepy Hollow Hotels of 2026

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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

Fairmont Chicago at Millennium Park

8/10 Good

"My wife was disappointed that the hotel did not provide room slippers or bathrobes. Upon cleaning the room, the bathroom products were not replaced/refilled. The cleaners did not replace the used coffee mugs."

The Chicago Hotel Collection - Magnificent Mile

8/10 Good

"Older property but locations is great! One block from miracle mile. Rooftop bar was great. Staff wonderful! Had a fitness center that I didn’t use but it was quite large with lots of equipment. The breakfast buffet was adequate but not spectacular. The bus stop is one block from hotel and runs frequently if you need to go downtown. Also can want subway station to go back and forth from airport. Lots of shops and restaurants nearby!"

Holiday Inn Chicago Dwtn - The Mart by IHG

4/10 Poor

"This hotel is on the brink, and it could go either up or down. The location is absolutely wonderful, right across the street from the Merchandise Mart, the beautiful RiverWalk, 1 block from some good restaurants and fun pubs. The waitstaff at the restaurant were excellent! However, in the room... broken towel bar. Repaired, but then drywall was left all over the bathroom and not cleaned, and they used our room towels (!!) while doing the repairs. So then we didn't have any clean towels, and had to keep calling over and over again, trying to get the room cleaned and fresh clean towels. Broken front door to the hotel, rather inconvenient esp with luggage. Thankfully the ADA compliant door worked well. Carpet was very sticky and the room smelled quite damp and musty. The furnishings were nicely updated, the bed linens were nice and clean, good pillows. The rooms and hallways were not well lit and felt gloomy. Beautiful views, but the windows were so dirty it was hard to see through them."

Congress Plaza Hotel

10/10 Excellent

"We able to checkin early for a small fee. Room was clean and good size. Shower was nice. Had shampoo conditioner and body wash. Sink was a little small for toiletries. Had a mini fridge and TV was fine. They stored our bags when leaving and concierge was very helpful. Very close to Millennial Park and had a great view for fireworks at Navy Pier. Close to the L if coming from Midway. A very nice stay"

Hilton Chicago

6/10 Okay

"I think the biggest drawback was the time to receive a service here. One night it took 4.5 hours for the service desk to connect to house cleaning to provide fresh bedding thus delaying our ability to get a good night’s sleep. The check-in line at night could be up to two hours to get checked in for new guests. We had to find our own clean towels daily."

Freehand Chicago

4/10 Poor

"My A/C was broke (and I was here in June), which I noticed as soon as I entered room. I notified desk on night 1, who said maintenance would address on day 2. Nothing was done day 2, so I went to front desk again. They said to come back day 3 morning and also gave me manager email for any complaints. I emailed manager and also went in day 3 morning to ask again if my A/C could be addressed, which they assured me it would. Yet again, when I came back to hotel day 3 evening it was not working. At this point I have up on the matter as it seemed to be a futile effort. Also, the manager never responded to my email from what is now about 4-5 days ago. No partial refund was given to me either for this issue."

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 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.

Hotels in Sleepy Hollow

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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

Fairmont Chicago at Millennium Park

Frequently asked questions

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