I was there last year for a conference. The river walk is a very nice way to take in some sights on your own. The lakefront trail is really nice to walk, too.
https://www.choosechicago.com/things...kefront-trail/
It's 18 miles long, but sights along it include:
Lincoln Park
Lincoln Park Zoo
Theater on the Lake
Soldier Field
South Shore Cultural Center
Museum of Science and Industry
McCormick Place
Grant Park
Monroe Harbor
Navy Pier
Jackson Park
Belmont Harbor
Burnham Park
Also you gotta get the deep dish. My favorite was this place:
https://www.yelp.com/biz/ord-pizzeri...eep+dish+pizza