Sleepy Hollow
Chicago
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Michigan Avenue
You can find the perfect gifts to bring home 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.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Things to do
Wendella's 90-min Chicago River Architecture Tour
Chicago By Night River & Lake Cruise
Chicago: Architecture Boat Tour with Drinks
Chicago: Navy Pier Centennial Wheel Ticket
Chicago River: 1.5-Hour Guided Architecture Riverboat Tour
Top hotels in Sleepy Hollow
Reviewed on 12 Jul, 2025
Reviewed on 13 Jul, 2025
Reviewed on 12 Jul, 2025
Reviewed on 13 Jul, 2025
Reviewed on 12 Jul, 2025
Reviewed on 13 Jul, 2025
Other neighbourhoods around Sleepy Hollow
Near West Side
Live music, theatres 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 Racine Station or Polk Station (Pink Line) to get around town.
West Loop
Consider a visit to Milwaukee Avenue 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
Soldier Field and Lake Michigan are a few top attractions in South Loop. Hop around the city on the metro at Roosevelt Station or Cermak-McCormick Place Station and check out the area's fascinating museums, panoramic lake views and popular shops.
Near South Side
Travellers choose Near South Side for its ample dining options. Hop aboard the metro at Cermak-McCormick Place Station or Roosevelt Station and check out top sights like Soldier Field.
West Town
Noted for its live music and theatres, 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.
Hyde Park
Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.