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29 Jul - 30 Jul
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Top Trending Hotels Near Sleepy Hollow, Chicago

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, (2072)
"Beautiful property, will definitely stay there again."
The price is ฿6,366
฿8,415 total
includes taxes & fees
21 Aug - 22 Aug
Sable at Navy Pier Chicago, Curio Collection by Hilton
Freehand Chicago
Cocktail bar

Freehand Chicago

4.0 star property
8.0 out of 10, Very good, (2132)
"Stayed many times, great fun!"
The price is ฿3,409
฿5,527 total
includes taxes & fees
24 Aug - 25 Aug
Freehand Chicago
Claridge House
Cocktail bar

Claridge House

4.0 star property
8.8 out of 10, Excellent, (1288)
"Great location & friendly staff."
The price is ฿13,710
฿17,048 total
includes taxes & fees
31 Jul - 1 Aug
Claridge House
Millennium Knickerbocker Chicago
Lobby lounge

Millennium Knickerbocker Chicago

4.0 star property
8.6 out of 10, Excellent, (1900)
"Great stay"
The price is ฿4,125
฿5,605 total
includes taxes & fees
24 Aug - 25 Aug
Millennium Knickerbocker Chicago
The Godfrey Hotel Chicago
American cuisine, al fresco dining

The Godfrey Hotel Chicago

4.5 star property
8.6 out of 10, Excellent, (1893)
"Great hotel in a great location. Would definitely stay again "
The price is ฿4,942
฿6,564 total
includes taxes & fees
24 Aug - 25 Aug
The Godfrey Hotel Chicago
The Chicago Hotel Collection Ambassador Gold Coast
Terrace/patio

The Chicago Hotel Collection Ambassador Gold Coast

4.0 star property
8.2 out of 10, Very good, (1061)
"Great location for shopping and dining. "
The price is ฿1,359
฿6,169 total
includes taxes & fees
4 Aug - 5 Aug
The Chicago Hotel Collection Ambassador Gold Coast
Hotel Chicago Downtown, Autograph Collection by Marriott
Meeting facility

Hotel Chicago Downtown, Autograph Collection by Marriott

4.0 star property
9.0 out of 10, Wonderful, (1001)
"the hotel was in an amazing location, very clean and comfortable for 4 people, and the beds were very comfortable!"
The price is ฿4,840
฿6,633 total
includes taxes & fees
14 Aug - 15 Aug
Hotel Chicago Downtown, Autograph Collection by Marriott
Thompson Chicago, by Hyatt
Restaurant

Thompson Chicago, by Hyatt

4.5 star property
9.0 out of 10, Wonderful, (1186)
"Great location and property!"
The price is ฿4,210
฿5,900 total
includes taxes & fees
24 Aug - 25 Aug
Thompson Chicago, by Hyatt
Congress Plaza Hotel
Banquet hall

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (9030)
"Great place to stay."
The price is ฿5,762
฿6,764 total
includes taxes & fees
4 Aug - 5 Aug
Congress Plaza Hotel
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, (3623)
"Great stay. "
The price is ฿5,080
฿5,963 total
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Chicago Downtown/Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile
Rooftop terrace

The Chicago Hotel Collection - Magnificent Mile

4.0 star property
7.2 out of 10, Good, (1139)
"Enjoyed staying here!"
The price is ฿1,318
฿6,121 total
includes taxes & fees
4 Aug - 5 Aug
The Chicago Hotel Collection - Magnificent Mile
Best Western Grant Park Hotel
Restaurant

Best Western Grant Park Hotel

2.5 star property
8.2 out of 10, Very good, (2598)
"Excellent Hotel!!"
The price is ฿4,003
฿4,699 total
includes taxes & fees
24 Aug - 25 Aug
Best Western Grant Park Hotel
Travelodge by Wyndham Downtown Chicago
Lobby

Travelodge by Wyndham Downtown Chicago

2.0 star property
7.2 out of 10, Good, (2282)
"Location, cleanness and staff were very good "
The price is ฿3,508
฿4,118 total
includes taxes & fees
25 Aug - 26 Aug
Travelodge by Wyndham Downtown Chicago
The Hoxton Chicago
3 bars/lounges, piano bar

The Hoxton Chicago

4.0 star property
9.0 out of 10, Wonderful, (1011)
"Excellent location and great vibe. "
The price is ฿6,789
฿7,969 total
includes taxes & fees
17 Aug - 18 Aug
The Hoxton Chicago
Hilton Chicago/Magnificent Mile Suites
Ballroom

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2567)
"Great location and hotel!"
The price is ฿4,666
฿5,477 total
includes taxes & fees
17 Aug - 18 Aug
Hilton Chicago/Magnificent Mile Suites
Holiday Inn Express Chicago - Magnificent Mile by IHG
Exterior

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 star property
8.4 out of 10, Very good, (1030)
"Great stay"
The price is ฿4,807
฿5,643 total
includes taxes & fees
17 Aug - 18 Aug
Holiday Inn Express Chicago - Magnificent Mile by IHG
Palmer House a Hilton Hotel
Ballroom

Palmer House a Hilton Hotel

4.0 star property
8.4 out of 10, Very good, (1818)
"What a wonderful place to stay"
The price is ฿5,632
฿7,424 total
includes taxes & fees
21 Aug - 22 Aug
Palmer House a Hilton Hotel
Hyatt Centric Chicago Magnificent Mile
Room, 1 King Bed, Corner | Premium bedding, pillow-top beds, in-room safe, desk

Hyatt Centric Chicago Magnificent Mile

4.0 star property
9.0 out of 10, Wonderful, (1021)
"Best place we have stayed in Chicago in a long time. "
The price is ฿5,494
฿7,403 total
includes taxes & fees
17 Aug - 18 Aug
Hyatt Centric Chicago Magnificent Mile
River Hotel
Lobby

River Hotel

4.0 star property
8.8 out of 10, Excellent, (4458)
"Great place to stay."
The price is ฿5,132
฿6,024 total
includes taxes & fees
7 Aug - 8 Aug
River Hotel
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, (3556)
"We had a great stay! "
The price is ฿3,883
฿4,558 total
includes taxes & fees
24 Aug - 25 Aug
The Whitehall Hotel, BW Premier Collection
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"."
Brian 2-night trip
Posted 12 hours ago
Hyatt Regency 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?

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.