Sleepy Hollow, IL
Chicago
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
McCormick Place
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Sleepy Hollow Hotel Deals
Congress Plaza Hotel
Very cool place to stay if you enjoy historic buildings. I would definitely stay here again. Clean room, walking distance to many places.
Reviewed on 2026/3/16
Hotel Riu Plaza Chicago
Great stay! No complaints! Breakfast buffet was a great plus!
Reviewed on 2026/3/15
Embassy Suites by Hilton Chicago Downtown River North
Nice location
Reviewed on 2026/3/16
Hilton Chicago/Magnificent Mile Suites
I searched and searched and searched for something to complain about and couldn't find a single thing lol The staff was amazing, the location was perfect, and the rooms were great!
Reviewed on 2026/3/15
Hilton Chicago O'Hare Airport
STAFF were excellent. Food in restaurant really delicious.
Reviewed on 2026/3/15
Hilton Chicago
Front desk staff seemed to speak to me as if I was inconveniencing their day when you work a front desk and your people coming in from out of the area, it’s important to offer a warm and welcoming tone. I did not experience that with said staff had a massive issue with parking that led to me having ...
Reviewed on 2026/3/15
Other neighborhoods around Sleepy Hollow
Near West Side
Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town.
West Loop
Consider a visit to Old St Patrick’s Church and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
South Loop
Known for its fascinating museums, panoramic lake views, and popular shops, there's plenty to explore in South Loop. Top attractions like Soldier Field and Lake Michigan are major draws. Catch the metro at Roosevelt Station or Cermak-McCormick Place Station to see more of the city.
West Town
Noted for its live music and theaters, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city.
Near South Side
Travelers choose Near South Side for its abundant dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
Wicker Park
Consider exploring the abundant dining options in Wicker Park. If sightseeing is on the list, Milwaukee Avenue is a top attraction. Hop on the metro at Damen Station or Division Station to see more of the area.
