I grew up outside of Chicago (and don't really feel especially settled any place else yet), so like
starrynight, I had a few of the BSC in my city in SS #14, although I don't think they did it justice.
(And I thought it was really rude of everyone else to be such brats when Claudia was at the Art Institute.)
Kristy: There's lots of sports in Chicago, but the most historically interesting place, especially for a baseball fan, is Wrigley Field (as opposed to U.S. Cellular Park, or whatever it is the White Sox play at now). Because I'm kind of a brat myself, I'm imagining Kristy getting into a loud argument with a Cubs fan, because really, Cubs fandom isn't so much about the play as it is a way of life.
Mary Anne: MA seems to have kind of a soft spot for things like going to the top of the Sears Tower, riding the ferris wheel at Navy Pier--very tourist-y things. I also have a feeling she would really like the Colleen Moore fairy castle (
www.msichicago.org/exhibit/fairy_castle/fchome.html ) at the Museum of Science and Industry. God, I loved that thing when I was little.
Claudia: The Art Institute again, of course, (the rest of them can go down and hang out in the children's room if they're going to act like babies--it was just ranked the best in the nation), but there are a bunch of other good art museums, too--the Museum of Contemporary Art, the Terra Museum of American Art, and all the college and university museums, especially the Oriental Institute at the University of Chicago.
Stacey: Lots of shopping, of course--I have a feeling Stacey would particularly like Michigan Ave, which isn't really my thing, but there are lots of privately owned boutiques if you get off the Magnificent Mile. A lot of really neat upscale consignment shops and vintage stores, too, although that may be more a Claudia thing. It's possible Stacey might try to be snobby about Chicago as compared to New York. This is a foolish thing to do.
(Although our mass transit is worse than NYC, and I will stipulate that.)
Dawn: The Field Museum and the Shedd Aquarium both have pretty heavy conservation/environmentalism slants in their exhibitions, as does the Brookfield Zoo (which technically isn't in Chicago proper, but whatever). There are a bunch of companies that do Chicago "ghost" tours, too--I've never been on one in Chicago, although I've been in other cities. Again, I'm a brat, and it would be pretty funny to get her onto one of the Upton Sinclair-styled tours of the meatpacking history of Old Chicago for the lol factor. (No, I've never taken one, but my brother had to for school. I've never even read
The Jungle all the way through.)
Mallory: Eh, what does Mallory do when they go places? Besides spend all her money on hair dye and make-up? In theory, Chicago has a terrifically rich literary history, but if Mal's still in her mice-in-hightops phase, she might not really appreciate that so much. I'm sure she could find some guy in a trenchcoat to suspect of being a mobster or something. (I'm serious--when I've traveled abroad and said I was in Chicago, one of the first things people say, still, is "Oh, Al Capone, yes?" and depending on how good their English is (or my whatever is), helpfully mime shooting a gun. So I can totally see Mal getting into Mafia fantasy spying).
Jessi: There's a lot of good dance in Chicago, and the Joffrey Ballet, as I understand it, is running in pretty close competition with the ABT this season. There are also a lot of black people, and you know, I hate to just say it like that, but Jessi's black. Seriously, though, there are lots of African and African-American focused theaters and dance troupes and concert halls, as well as museum exhibits and tours and stuff.
Abby: I feel old, because I don't remember if they have an age restriction for all the shows at Second City (I know some of them do--it's not 21, because I went when I was in my late teens), but there are a bunch of other Chicago-based improv troupes, too.