My relationship with Chicago has been a tricky one. I never had very much interest in visiting it until I got into a friendly to-an-fro with a coworker in Chicago who would tell me its better than New York City. My go-to comeback was Chicago’s nickname of “Second City,” second to New York of course. When I finally decided to visit, I went with the intention to not like it as much as New York just to prove a point (I’m stubborn like that), but I was very pleasantly surprised. Its often referred to a clean version of New York, but I see it with its own unique and inescapable charm.