Your tips Do the waterfront boat tours ,and the Architectural tours are well worth it. Or just wander and enjoy the sights. Free stuff on at all times of the year and plenty of info is available.
Chicago is an amazing city, clean well ordered and welcoming. Easy to find your way around and plenty of cheap good food to be had. We visit family in a nearby town and travel in to the city by excellent train systems. The water front is beautiful, and plenty of venues to see. Summer time in particular. Jazz festival amazing in the late summer and most of it free to see . People friendly and I have walked around and back to the train alone and felt safe. Go visit if on a stopover it is well worthwhile. Watching the city light up from the Hancock tower is great,and free to go up if you are buying a cocktail. Visit the Cheesecake factory at the base !