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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
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
Sleepy Hollow Hotel Deals
Reviewed on Jul 8, 2025
Reviewed on Jul 7, 2025
Reviewed on Jul 8, 2025
Reviewed on Jul 9, 2025
Reviewed on Jul 5, 2025
Reviewed on Jul 7, 2025
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 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
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.
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.
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.
Hyde Park
Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.
- Wrigley Field
- Navy Pier
- Michigan Avenue
- Millennium Park
- Grant Park
- Chicago Riverwalk
- Lake Michigan
- Soldier Field
- United Center
- University of Chicago
- Northwestern University
- Donald E. Stephens Convention Center
- Willis Tower
- Merchandise Mart
- Loyola University Chicago
- Chicago Theatre
- Allstate Arena
- State Street
- University of Illinois Chicago
- Chicago Museum of Science and Industry
- Lincoln Park Zoo
- Rosemont Theatre
- Water Tower Place
- Northwestern Memorial Hospital
- John Hancock Center