I live in Chicago have lived here for fifty years (in the actual city, not the suburbs). I think it is the greatest city in the world. Many things to do and see and more great restaurants than you could visit in a lifetime. And yes, like all major cities there are parts that you would not want to be in. I agree with some of the previous posters it is better to take public transport to get around the city, especially when you are visiting the city center. If you must drive into the city. Your parking choices street parking or surface parking lots. There are mostly parking structures in the area around Willys (by the way we Chicagoans still refer to the building as Sears Tower) with very low clearance (<7'-0"). All street parking is paid parking by the quarter hour, I believe with a maximum parking limit of two hours. I would not park there unless you get lucky and find a really large spot to pull into. There are some surface parking lots just across the river to the west of Willys Tower, in Greek town. You could park there. You can usually park for about $20 for the day and walk to Willys it is around a mile walk. The nice thing about parking here is that you are in the middle of Greek Town. This area is along Halsted St. just to the west of downtown and Willys. This area is famous for the many great Greek restaurants that are located here. All of them very authentic. I would highly suggest lunch or dinner there. There are five main restaurants along this strip, all of them are on my recommended list. Make sure you get the flaming cheese appetizer when you go there. This dish was invented in Chicago at the Parthenon restaurant. The Parthenon is my favorite but a bit more upscale than the other four. Personally for me, Giordano's and the other famous place Gino's East are over rated (tourist place). Personally I like Connie's pizza myself.
The whole area is very congested especially during the week and the drivers are pretty aggressive, especially around RVs.
As far as camping pezvela is on the money about Illinois Beach State Park and Chain o' Lakes State Park. Water and dump stations are open by the end March early April. If you have any questions PM me.