We went to Chicago with our kids in the winter time. Sounds crazy to visit the windy city at this time but my husband had a conference there so we tagged along. I knew I wanted to eat deep dish pizza and go up the Willis Tower. Other than that I wasn’t sure what Chicago had to offer. It turns out there are a lot of things to do there. We were there for three full days. The first two days I did by myself with the kids and the last day Matt was able to join us.