If you want deep dish pizza, one of my favorite places is Pequod's on Webster and Clybourn. If you're staying downtown there's a bunch of "Chicago style" places to choose from. Lou Malnati's or Gino's East are good. If you want thin crust, then head to Bricks on Wisconsin and Lincoln in Old Town. It's a neat hole in the wall with fantastic pizza. My favorite pie in the city. I recommend checking out some Improv or sketch comedy while you're down there. IO (formerly Improv Olympic) on Clark about half block from Wrigley has shows 7 days a week and the quality is consistently good. And it's affordable. I think the mainstage is like $14 per person. Second City is on North and Wells in Old Town is also consistently good but it's a bit more money and you have to get your tickets well in advance especially for a weekend show. One tour I've always wanted to do is the Gangster bus tour of Chicago. They take you around and show you all the famous hangouts of guys like Capone and Frank Nitti and I believe you also see sites of famous murders and shoot outs (e.g. spot where Dillinger was killed, site of St. Valentine's Day Massacre, etc.) Getting around via mass transit is really easy. I'd buy a three day pass at one of the El stations. If you want to know the best route to take to get from A to B via bus/train head to this site: http://www.transitchicago.com/ And use the Trip Planner. All buses have GPS linked to this web site: www.ctabustracker.com so you can check on your phone how long it will be for a bus to arrive at your stop. Very useful.