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Top Trending Hotels Near Sleepy Hollow, Chicago

River Hotel
Elevators lead to upper floors from this grand corridor, flanked by ornate columns.

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4501)
"Great stay and great location"
The price is ฿5,400
฿6,339 total
includes taxes & fees
17 Aug - 18 Aug
River Hotel
DoubleTree by Hilton Chicago - Magnificent Mile
Relax by the pool surrounded by lounge chairs and umbrellas, taking in the city skyline views.

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1966)
"Great place !"
The price is ฿5,148
฿6,043 total
includes taxes & fees
1 Sept - 2 Sept
DoubleTree by Hilton Chicago - Magnificent Mile
Eurostars Magnificent Mile
Enjoy a meal with a view at this restaurant, offering a variety of seating options and a central bar area.

Eurostars Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (3061)
"Great stay!"
The price is ฿5,174
฿6,073 total
includes taxes & fees
11 Aug - 12 Aug
Eurostars Magnificent Mile
Sable at Navy Pier Chicago, Curio Collection by Hilton
Relax in style with lounge chairs and bar stools amidst a scenic backdrop.

Sable at Navy Pier Chicago, Curio Collection by Hilton

4.0 star property
9.4 out of 10, Exceptional, (2061)
"Beautiful property, will definitely stay there again."
The price is ฿5,277
฿7,132 total
includes taxes & fees
1 Sept - 2 Sept
Sable at Navy Pier Chicago, Curio Collection by Hilton
citizenM Chicago Downtown
Experience the vibrant city atmosphere in this urban oasis, featuring a striking geometric-patterned awning and modern architecture.

citizenM Chicago Downtown

4.0 star property
9.2 out of 10, Wonderful, (3535)
"Would love to stay here again!"
The price is ฿5,057
฿5,937 total
includes taxes & fees
26 Aug - 27 Aug
citizenM Chicago Downtown
Congress Plaza Hotel
Experience grandeur in this beautifully designed ballroom with high ceilings, arched windows, and elegant table settings.

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8926)
"Great place to stay."
The price is ฿8,120
฿9,532 total
includes taxes & fees
7 Sept - 8 Sept
Congress Plaza Hotel
Best Western River North Hotel
Relax on the rooftop with wicker lounge chairs and take in the city skyline views.

Best Western River North Hotel

2.5 star property
7.8 out of 10, Good, (1027)
"Great location "
The price is ฿4,095
฿4,808 total
includes taxes & fees
24 Aug - 25 Aug
Best Western River North Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Experience the sleek, modern architecture of this urban hotel, featuring a prominent marquee sign and vertical windows.

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
8.4 out of 10, Very good, (3640)
"Great stay. "
The price is ฿4,962
฿5,825 total
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Hilton Chicago
Classic hotel with a symmetrical facade and central entrance.

Hilton Chicago

4.0 star property
8.4 out of 10, Very good, (2055)
"Enjoyed our stay. Great location."
The price is ฿4,524
฿6,260 total
includes taxes & fees
2 Sept - 3 Sept
Hilton Chicago
Crowne Plaza Chicago West Loop by IHG
Relax in a casual, urban setting with seating areas and a prominent counter for ordering.

Crowne Plaza Chicago West Loop by IHG

3.5 star property
8.8 out of 10, Excellent, (1362)
"Staff was so friendly and the rooms were really clean!"
The price is ฿4,592
฿5,390 total
includes taxes & fees
24 Aug - 25 Aug
Crowne Plaza Chicago West Loop by IHG
Aloft Chicago Mag Mile
Conference room with a large, round table and six chairs, offering city views.

Aloft Chicago Mag Mile

3.0 star property
8.6 out of 10, Excellent, (2783)
"We love our stay here !"
The price is ฿4,495
฿5,276 total
includes taxes & fees
24 Aug - 25 Aug
Aloft Chicago Mag Mile
Freehand Chicago
Relax in style with plush seating and a classic design, featuring a sofa, armchairs, and a bookshelf.

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2175)
"Good spot when staying for lolla "
The price is ฿3,609
฿4,806 total
includes taxes & fees
20 Aug - 21 Aug
Freehand Chicago
Holiday Inn & Suites Chicago - Downtown by IHG
Relax by the rooftop pool with a stunning view of the city skyline.

Holiday Inn & Suites Chicago - Downtown by IHG

3.0 star property
8.4 out of 10, Very good, (1010)
"I was happy with my stay. Clean rooms and friendly staff"
The price is ฿4,786
฿6,006 total
includes taxes & fees
3 Sept - 4 Sept
Holiday Inn & Suites Chicago - Downtown by IHG
Hilton Chicago/Magnificent Mile Suites
Enjoy a sophisticated dining experience with a beautifully set table and city view.

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2595)
"Great location and hotel!"
The price is ฿4,645
฿5,453 total
includes taxes & fees
24 Aug - 25 Aug
Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection River North
Enjoy a casual coffee break in our cozy coffee shop with a menu board, seating area, and unique decor.

The Chicago Hotel Collection River North

3.0 star property
7.2 out of 10, Good, (544)
"It was a wonderful place to stay! "
The price is ฿2,180
฿5,211 total
includes taxes & fees
21 Aug - 22 Aug
The Chicago Hotel Collection River North
The Whitehall Hotel, BW Premier Collection
Relax in a spacious room with a large bed, a smaller bed, and a comfortable seating area.

The Whitehall Hotel, BW Premier Collection

3.5 star property
8.2 out of 10, Very good, (3522)
"Excellent location, renovated rooms, easy access and near attractions"
The price is ฿3,722
฿4,370 total
includes taxes & fees
2 Sept - 3 Sept
The Whitehall Hotel, BW Premier Collection
La Quinta Inn & Suites by Wyndham Chicago Downtown
Experience the vibrant city at La Quinta Inn & Suites, offering a variety of rooms with city views.

La Quinta Inn & Suites by Wyndham Chicago Downtown

3.0 star property
8.6 out of 10, Excellent, (2464)
"Had a wonderful stay here and staff was super friendly!"
The price is ฿4,627
฿6,002 total
includes taxes & fees
24 Aug - 25 Aug
La Quinta Inn & Suites by Wyndham Chicago Downtown
Travelodge by Wyndham Downtown Chicago
Relax in the hotel lobby's spacious seating area, surrounded by a city view and comfortable sofas and armchairs.

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2281)
"Hotel location, staff and transportation were very good "
The price is ฿3,085
฿3,621 total
includes taxes & fees
25 Aug - 26 Aug
Travelodge by Wyndham Downtown Chicago
Hyatt Centric The Loop Chicago
Experience the city from a modern high-rise hotel with panoramic views from the interior.

Hyatt Centric The Loop Chicago

4.0 star property
9.0 out of 10, Wonderful, (2022)
"Love staying here "
The price is ฿5,871
฿6,892 total
includes taxes & fees
21 Aug - 22 Aug
Hyatt Centric The Loop Chicago
Silversmith Hotel Chicago Downtown
Experience the sleek lobby with a reception desk, black metal railings, and a geometric patterned wall.

Silversmith Hotel Chicago Downtown

4.0 star property
9.4 out of 10, Exceptional, (1929)
"Very nice and comfortable stay"
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.
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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 map

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 map

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 map

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 map

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 map

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
"Downtown close to all shopping and excellent restaurants. Highly recommend "
Kathleen 2-night trip
Posted 16 hours ago
The Whitehall Hotel, BW Premier Collection

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?

Places you might want to visit in the area around Sleepy Hollow include Hawthorne Works Museum and Balzekas Museum of Lithuanian Culture. When you're sightseeing around the area, United Center and Bridgeport Art Center are a couple of other sights to visit.