It’s been 6 (!) years since I lived there but in the last few weeks several friends have asked me for tips on Chicago, so I figured I might as well post them here too:
So Chicago. First, don’t stay in the South Side. It really is the ghetto. Visiting the University of Chicago (my alma mater!) for an afternoon could be nice: the campus and architecture is pretty, the Sem Coop is an awesome bookstore, Robie House is a Frank Lloyd Wright masterpiece, and the Field and the Oriental Museums are surprisingly good. You could make it an evening with dinner at the Med (http://www.medici57.com/), a movie at Doc Film (http://docfilms.uchicago.edu/dev/), and then a beer at The Pub (https://studentactivities.uchicago.edu/services/pub.shtml; Monday is Wing Night!) or Jimmy’s (http://www.yelp.com/biz/woodlawn-tap-chicago). Beyond the university, though, there’s no real reason to go south of the Loop, though the White Sox have good cheap tickets. The #6 bus is probably the best way to get to Hyde Park (https://familyweekend.uchicago.edu/directions.shtml) unless you’re by a Green Line or Metra stop. The Red Line stops far away and you have to take the notoriously unreliable #55 bus…
So, then the question is whether to stay in the Loop, near the Magnificent Mile, or somewhere else. The Loop is boring – it’s all office buildings – but there are a bunch of hotels there and you are near the Art Institute (a fantastic museum, definitely worth visiting). Millennium Park and the CSO (http://cso.org/) are also there. If Will (http://cso.org/About/Performers/Performer.aspx?id=6158) is in the house, say hi for me.
The Magnificent Mile is more touristy, both in a good and bad sense. There are lots of hotels (the Drake is a classic old place), shopping, and restaurants (but there are also some nice places sprinkled throughout the Loop), However, since it’s touristy is can seem a little bland and generic. The MCA (http://www.mcachicago.org/) is nearby, though, and pretty cool.
Chicago has very distinct neighborhoods, so you may want to stay a bit out of the center and get more of the local experience. For instance, Wrigleyville has lots of sports bars and clubs (because it surrounds the Cubs’ ballpark, Wrigley Field), while Andersonville is the old Swedish neighborhood. (It isn’t anymore but it’s still nice and fun to hang out – it’s a good place for brunch on the weekend.) Wicker Park is also popular. Pislen’s entirely Mexican and has great food. Chinatown (http://en.wikipedia.org/wiki/Chinatown,_Chicago) can also be nice for a meal.
Finally, as you may know, Chicago is known for improv, with lots of people from Saturday Night Live coming from Second City (http://www.secondcity.com/) and places like that. Well worth the ticket.
Oh, and FOOD! Go to Portillo’s (http://www.portillos.com/portillos/) for a hot dog and Giordano’s (http://www.giordanos.com/) for a pizza. There are also plenty of great steakhouses (I’m trying to remember the classic one I went to my old boss and am failing). There are also lots of good Italian restaurants, like Topo Gigio that I went to with my mom (http://www.topogigiochicago.com/). If for some reason you find yourself REALLY far north (http://www.hotdougs.com/) or south (http://en.wikipedia.org/wiki/Maxwell_Street_Polish; there are places all over the DEEP South Side called Maxwell Street or The Depot serving them and similar things) there are some crazy options. There also good restaurants that aren’t just hot dogs or pizza or steak.