Woodlawn Travel Guide
Tourist Guide
Popular places to visit
Jackson Park
Jackson 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 galleries.
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.
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.
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Activities
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour
Chicago Crime and Mob Bus Tour
Our pick of the best Woodlawn Hotel Deals
Congress Plaza Hotel
Friendly staff. Clean room.
Reviewed on 5 Feb 2026
Hilton Chicago
Great location and great hotel!
Reviewed on 3 Feb 2026
DoubleTree by Hilton Chicago - Magnificent Mile
Close to everything!! The staff were super friendly. I would book again when in Chicago.
Reviewed on 2 Feb 2026
Embassy Suites by Hilton Chicago Downtown River North
Clean, and great service
Reviewed on 6 Feb 2026
Hotel Riu Plaza Chicago
Yes
Reviewed on 4 Feb 2026
Hilton Chicago/Magnificent Mile Suites
Such great service, room was clean, and hotel staff were amazing! 10/10 recommend and will be staying here again when we come back!
Reviewed on 4 Feb 2026
Other neighbourhoods around Woodlawn
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.
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.
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 of the city at Washington Station or Monroe Station (Blue Line).
The Loop
Michigan Avenue and Lake Michigan 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.
Near West Side
Live music, theatres and shopping highlight some notable features of Near West Side. Make a stop by Credit Union 1 Arena or United Center while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town.
Downtown Chicago
Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
