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Top Trending Hotels Near Sleepy Hollow, Chicago

River Hotel
Lobby

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4560)
"Great place to stay, staff was very friendly"
The price is £95
includes taxes & fees
14 Sept - 15 Sept
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, pool loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (2011)
"Pool area and deck were great for the family, beds were comfortable, location is great."
The price is £131
includes taxes & fees
1 Sept - 2 Sept
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Reception

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3065)
"Great stay!"
The price is £153
includes taxes & fees
25 Aug - 26 Aug
Eurostars Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Terrace/patio

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2089)
"Great place to stay!"
The price is £163
includes taxes & fees
1 Sept - 2 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Exterior

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (3751)
"Great place to stay "
The price is £124
includes taxes & fees
2 Sept - 3 Sept
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8996)
"Family had a great stay. "
The price is £103
includes taxes & fees
25 Aug - 26 Aug
Congress Plaza Hotel
Aloft Chicago Mag Mile
Meeting facility

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2800)
"Clean, helpful staff and in walking distance to most places we visited."
The price is £112
includes taxes & fees
1 Sept - 2 Sept
Aloft Chicago Mag Mile
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2237)
"Great stay "
The price is £90
includes taxes & fees
3 Sept - 4 Sept
Freehand Chicago
citizenM Chicago Downtown
Terrace/patio

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3636)
"Great place"
The price is £132
includes taxes & fees
3 Sept - 4 Sept
citizenM Chicago Downtown
Best Western River North Hotel
Rooftop terrace

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1033)
"Great location "
The price is £106
includes taxes & fees
25 Aug - 26 Aug
Best Western River North Hotel
Holiday Inn & Suites Chicago - Downtown by IHG
Seasonal outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very good, (1008)
"Friendly staff and close to the places I wanted to go to "
The price is £140
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn & Suites Chicago - Downtown by IHG
Crowne Plaza Chicago West Loop by IHG
American cuisine

Crowne Plaza Chicago West Loop by IHG

3.5 star property
8.8 out of 10, Excellent, (1407)
"Bernell was awesome at check in!! Would definitely recommend this Hotel!!!"
The price is £155
includes taxes & fees
1 Sept - 2 Sept
Crowne Plaza Chicago West Loop by IHG
FOUND Hotel Chicago River North
Exterior

FOUND Hotel Chicago River North

2.0 star property
8.2 out of 10, Very good, (207)
"Great place "
The price is £81
includes taxes & fees
1 Sept - 2 Sept
FOUND Hotel Chicago River North
La Quinta Inn & Suites by Wyndham Chicago Downtown
Exterior

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2496)
"Had a wonderful stay here and staff was super friendly!"
The price is £129
includes taxes & fees
1 Sept - 2 Sept
La Quinta Inn & Suites by Wyndham Chicago Downtown
Regal Inn - Chicago O'Hare Airport
Lobby

Regal Inn - Chicago O'Hare Airport

2.0 star property
8.0 out of 10, Very good, (1007)
"Was a nice place with a great restaurant right around the corner. Would stay again. "
The price is £57
includes taxes & fees
25 Aug - 26 Aug
Regal Inn - Chicago O'Hare Airport
The Whitehall Hotel, BW Premier Collection
1 bedroom, Egyptian cotton sheets, premium bedding, pillow-top beds

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very good, (3552)
"Again a really nice, clean, good for familys hotel."
The price is £96
includes taxes & fees
2 Sept - 3 Sept
The Whitehall Hotel, BW Premier Collection
Hyatt Centric The Loop Chicago
Rooftop terrace

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2056)
"Very good place "
The price is £169
includes taxes & fees
1 Sept - 2 Sept
Hyatt Centric The Loop Chicago
Hotel Riu Plaza Chicago
Front of property

Hotel Riu Plaza Chicago

4.0 star property
9.4 out of 10, Exceptional, (2334)
"The best hotel, excellent breakfast, excellent location!!!"
The price is £144
includes taxes & fees
2 Sept - 3 Sept
Hotel Riu Plaza Chicago
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Lobby

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3.0 star property
8.4 out of 10, Very good, (2078)
"We had a great stay!"
The price is £145
includes taxes & fees
3 Sept - 4 Sept
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Silversmith Hotel Chicago Downtown
Lobby

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1953)
"Great room and close to attractions "
Silversmith Hotel Chicago Downtown
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.

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas for the activities you enjoy most.
Downtown Chicago featuring a city

Downtown Chicago

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Magnificent Mile - River North

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

The Loop - Downtown featuring a river or creek

The Loop

Michigan Avenue and Lake Michigan are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

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.

Chicago featuring a city and modern architecture

Lincoln Park

Known for its ample dining options and fantastic lake views, there's plenty to explore in Lincoln Park. You can visit top attractions like Lake Michigan and Lincoln Hall, and jump on the metro at Fullerton Station or Armitage Station to see more of the city.

Top Sleepy Hollow Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"I had a great time. We requested a microwave be brought to our room and it was delivered in a few minutes. The breakfast was reaaly nice. We enjoyed walking in the area around the hotel. It was a great stay. "
Shelly 2-night trip
Posted 19 hours ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

What are the best family hotels in Sleepy Hollow?
The Carlton Inn Midway in Chicago is a fantastic option for families seeking comfort and convenience during their travels. This family-friendly hotel offers complimentary cribs and free stays for children, making it an excellent choice for those traveling with little ones.
What hotels in Sleepy Hollow offer free breakfast?
Carlton Inn Midway in Chicago is an excellent choice for travellers seeking a family-friendly atmosphere with convenient amenities. This welcoming hotel offers a complimentary continental breakfast, ensuring that families can start their day off right without any hassle. The 24-hour airport shuttle service makes it easy for guests to navigate their travel plans, great for families arriving with little ones in tow.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Sleepy Hollow.
How can I save on a Sleepy Hollow hotel booking with Expedia?
Members always get our best prices. Find our best Sleepy Hollow hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Sleepy Hollow hotel?
Hotel prices in Sleepy Hollow often vary, but you can find a great deal from £81 on Expedia. Different factors affect nightly hotel rates, such as the time of year or the days of the week you want to book. To find the best deals for your stay, be flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.