We had some things in mind as to what we wanted to do in Chicago but Caroline also had some suggestions that helped. Caroline gave us a Lyft discount code, useful after a long day of walking around and being rained on. After that we got to sit on the couch and enjoy some Netflix and the antics of Carolines dog.
If you want to head into downtown you've got plenty of options; you can drive, take a bus, take the train, or use Uber/Lyft. There are also plenty of places to eat close by, easily within 10 minutes of walking.
All in all I would recommend staying with Caroline, she's very easy going and you can't beat the price!