Woodlawn Travel Guide
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
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
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.
Navy Pier
With a visit to Navy Pier, a favourite shopping spot in Chicago, you can search for that perfect souvenir. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
McCormick Place
During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.
Soldier Field
Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.
Top hotels in Woodlawn
Congress Plaza Hotel
Wonderful hotel
Reviewed on 4 Feb 2026
Embassy Suites by Hilton Chicago Downtown River North
Positives- As my friend said as we went to breakfast “the people here are so nice and look happy to work here!” I agree! Eloisa (I hope that is correct-our bartender ) made happy hour on Friday night even happier! She was friendly and knowledgeable, suggesting drinks we hadn’t had before just by ...
Reviewed on 8 Feb 2026
Hotel Riu Plaza Chicago
Love the room! Very ritzy!!
Reviewed on 8 Feb 2026
Hilton Chicago
Great location and great hotel!
Reviewed on 3 Feb 2026
Aloft Chicago Mag Mile
it was good
Reviewed on 3 Feb 2026
Hilton Chicago/Magnificent Mile Suites
The hotel was good but it could’ve been a bit cleaner. I had a bit of a musty smell, the toilet had a permanent stain and it was very dusty. I reached out to the front desk about the smell and they came to freshen up the room. The service and location are a big plus so I would probably stay ...
Reviewed on 9 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.
