I dont really like big cities and chicago is a driving nightmare. Toll roads all over. Was just there for a wedding (flew out), rented a vehicle and used a navigator to get all over since roads go to places never heard of. Anyhow, find an rv park/campground, rent a car/truck and then try to figure out where you want to go. we have been in all he tall buildings, along lake shore, taken the river cruise. So just need to figure out what you want to seen and how to get there to see it.DO NOT try to park in chicago itself, you will need to get the rv parked somewhere in the subburbs.