Woodlawn, IL
Chicago
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 fascinating museums.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
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.
Soldier Field
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Things to do
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour
Chicago River: 1.5-Hour Guided Architecture Cruise
Woodlawn Hotel Deals
Congress Plaza Hotel
Great location, beautiful historic hotel with clean, updated rooms.
Reviewed on Feb 11, 2026
Hotel Riu Plaza Chicago
The great customer service, clean room, and enjoyed the free breakfast.
Reviewed on Feb 11, 2026
Embassy Suites by Hilton Chicago Downtown River North
Staff was very warm and welcoming. Breakfast was delicious. The pool was very nice but needs to be shocked every week or after alot of swimmers have been in the pool! Absolutely loved valet, that was definitely a plus. And most of everything you wanna do in Chicago is right next to the hotel!!
Reviewed on Feb 11, 2026
Hilton Chicago
Outdated rooms and our heater stopped working overnight and the temp fell to 60's which felt freezing given it was zero outside with snow flurries But Matt the maintenance guy came quickly at 6 am thankfully and got it back up and running. Other than that, a truly beautiful hotel and the restaurant ...
Reviewed on Feb 8, 2026
Aloft Chicago Mag Mile
Everything was awesome at this hotel. From the attention and care of the desk staff to the fabulousness of the room and valet. Really great. Happy to stay there again.
Reviewed on Feb 10, 2026
Hilton Chicago/Magnificent Mile Suites
Spacious. Clean and great location
Reviewed on Feb 11, 2026
Other neighborhoods around Woodlawn
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.
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.
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
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
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 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.
Woodlawn, IL
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- Lorado Taft's Midway Studios
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