I grew up near Chicago and still live in IL, probably going to the city on average once a year. Having said that, I've done most of the major things there: Michigan Ave, State St, Navy Pier, John Hancock, Shedd, the planetarium, the Field Museum, art museum, and Science and Industry.
My husband and I are going for a weekend in late March for my birthday, and I was wanting to find some other, different things to do for 1.5 days. We do plan on going to an 11 PM show at Second City, but otherwise, have no plans. We're staying at the Dana Hotel but are fine with taking a cab or walking (we will have a car but driving and parking in Chicago is a royal pain).
Any neat neighborhoods, shops, or restaurants?