I've been to Chicago three or four times now and always seem to come across some little gem or other, its a great place. I always have to stop off for a deep-pan pizza, a Chicago-style hot dog and try to make time for a comedy show - the 'Second City' comedy club is world-famous for its improv. I really like the city's laid-back (compared to, say, New York), Midwestern feel and there's a certain charm, as well as sadness, to its rust-belt.
Although this was sadly just a short visit, I came across one or two places I wanted to share:
Kinda like an up-market diner, this place offers incredible modern versions of old-school American classics. I ordered Bone Marrow & Ox Tail Marmalade - which was honestly one of the most intense, lip-smackingly good things i've eaten in a while. I'm also glad that I stole a bite of the burger, it was fantastic. Aside from the amazing food, they make some pretty mean cocktails (I think we worked our way through all of them). The Hemmingway was particularly good as were the several Picklebacks (a shot of Whisky followed by a shot of pickle juice) that washed it all down.
We also took in the views at the bar on top of the John Hancock tower. The bar itself isn't anything special but the view from the 96th floor is great; you can see the whole city and over the Great Lakes to Indiana.