Chicago is a favorite of mine. I could never live there. As a sheltered Californian, weather is a cut. Nevertheless Chicago is one of the most architecturally beautiful cities in the world, filled with warm and excellent people.
I like to think of it as the city with all the pluses of NYC, with none of the douchebags. I also appreciated everyone's willingness to lay on the horn in Chicago. People in California drive like utter shit and I'm convinced it's because they're never publicly shamed by a horn.
I've been to Chicago 2 times, and both times I've wanted to take a river tour and wasn't able to. Next time I'll make the effort to get on the water.
I did manage to make it to the top of the John Hancock building this time. Great view for the sunny Sunday I got to enjoy in March,