I disliked the native Chicagoites very much. There was a blatant fake vibe to them. They always try to impress and lay on the BS as if people have no idea. I won’t miss that crowd.
That town must have changed a lot in the last 25-30 years. During the late 80's, early 90's I traveled to Chicago pretty regularly, and I loved the music scene along Rush & Division, and unlike L.A. where everyone dresses casual 24-7, working Chicagoans dressed with real class, and the nightlife was quite impressive. Now I'm sure weather was the big influence on how they dressed, and that weather during the winter is something I never want to experience again, but the way the city lit up around the Christmas season does leave a nice memory.
Unfortunately, the crime I've been reading about in Chicago over the last decade plus leaves me with zero interest in returning.