Sleepy Hollow, IL
Chicago
Visit Sleepy Hollow
Popular places to visit
Wrigley Field
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Navy Pier
With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
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
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the fascinating museums and notable monuments in this vibrant area.
Millennium Park
After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Grant Park
Grant Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene.
Sleepy Hollow Hotel Deals
Reviewed on 8 July 2025
Reviewed on 9 July 2025
Reviewed on 8 July 2025
Reviewed on 9 July 2025
Reviewed on 5 July 2025
Reviewed on 9 July 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.
- Places of interest
- Sleepy Hollow Hotels by Star Rating
- Hotels in top Chicago neighborhoods
- Sleepy Hollow Hotels by Brand
- Wrigley Field
- Navy Pier
- Michigan Avenue
- McCormick Place
- Millennium Park
- Grant Park
- Chicago Riverwalk
- Lake Michigan
- Soldier Field
- United Center
- University of Chicago
- Northwestern University
- Art Institute of Chicago
- Donald E. Stephens Convention Center
- Willis Tower
- Merchandise Mart
- Loyola University Chicago
- Chicago Theatre
- Allstate Arena
- State Street
- University of Illinois Chicago
- Field Museum of Natural History
- Chicago Museum of Science and Industry
- Rate Field
- Lincoln Park Zoo
- Rosemont Theatre
- Wintrust Arena
- Water Tower Place
- SeatGeek Stadium
- Northwestern Memorial Hospital
- Cloud Gate
- John Hancock Center