Popular places to visit
Jackson Park
Explore the great outdoors at Jackson Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.
63rd Street Beach
Why not spend a lazy afternoon at 63rd Street Beach during your trip to Chicago? Wander the beaches and gardens while you're in the area.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
Things to do
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Woodlawn Hotel Deals
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Other neighborhoods around Woodlawn
Hyde Park
Hyde Park is noteworthy for its museums, and you can make a stop at top attractions like Lake Michigan and Robie House.
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 Grant Park.
South Loop
Known for its fascinating museums, panoramic lake views, and popular shops, there's plenty to explore in South Loop. Top attractions like Grant Park and Soldier Field are major draws. Catch the metro at Roosevelt Station or Cermak-McCormick Place Station to see more of the city.
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.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
The Loop
Grant Park and Millennium Park 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.
More to Explore
- Places of interest
- Woodlawn Hotels by Star Rating
- Hotels in top Chicago neighborhoods
- Woodlawn Hotels by Brand
- Other vacations you might like
- Jackson Park
- Lorado Taft's Midway Studios
- Bob-O-Link Meadow
- Wrigley Field
- McCormick Place
- Navy Pier
- Grant Park
- Millennium Park
- Soldier Field
- Michigan Avenue
- United Center
- Indiana Dunes National Park
- Chicago Riverwalk
- Art Institute of Chicago
- Lake Michigan
- Northwestern University
- Willis Tower
- University of Chicago
- Donald E. Stephens Convention Center
- Field Museum of Natural History
- Chicago Theatre
- Loyola University Chicago
- Chicago Museum of Science and Industry
- University of Illinois Chicago
- Lincoln Park Zoo
- Hollywood Casino Amphitheatre
- Merchandise Mart
- Hard Rock Casino Northern Indiana
- SeatGeek Stadium
- John Hancock Center