The Chicago History Museum seems to be a very interactive and detailed museum (though I've never been there) about the city's interesting past. The museum has a permanent exhibit called Chicago: Crossroads of America, which details the history of the city. One of the main focuses of the exhibit is Chicago as the transportation center and connecting point between the East and the West, as we discussed in class with the railroads. The exhibit has models of the towns and ships used, and original trains and L-trains that you can climb aboard.
On the site there are links to articles explaining and detailing the transportation history of Chicago, especially the transformation of Chicago into a major metropolis. One link from the page, from the Encyclopedia of Chicago, entitled Transportation described the advantages of Chicago's railways and location: "More significant was Chicago's role as the principal transshipment point between eastern and western rail networks. No city before or since assumed such a strategic position." After the train history that we learned, it also describes the development of the L-trains and buses, allowing for greater intra-city movement, and later the effect of airplanes and cars on the rail industry and transportation in general.
Part of the history of Chicago exhibit includes "In Our Own Words Teen Audio Tours" by students, about many aspects of Chicago's history. Some that were connected to our readings were the Haymarket riot. Students discuss the Haymarket memorial and explain how and why the Haymarket affair came to be. The student explaining the incident explained that eight anarchists were arrested, without a link to the actual event, and that the newspapers clearly lauded the police action (so we can kinda tell whose "side" the student seems to be on). They also have a segment on a fictional Great Migration story: a woman lived on a farm in the south, and the Chicago Defender made North sound great--the "Promised Land", no segregation, lots of jobs. So the woman in the story and her family saved up for train tickets and went to Chicago, where the streets were filthy and packed. The husband worked in industry and there wasn't very much money, despite the "golden opportunities" they had heard about, and there was still segregation and hatred between blacks and whites. They then explained the race riot of 1919 between whites and blacks, and said that despite the federal troops breaking up the riots the tension was not gone.
Also, many celebrations of Chicago in art and music, but some representations show the darker sides: the seamy "underbelly" of corruption and murder in the musical & movie Chicago, and the cold and poor aspect of the ghetto in "In the Ghetto" by Apache Indian.