I’m leaving for Chicago this June to visit relatives for a couple of weeks – they’ve got a lot of stuff planned, but I don’t wanna miss out on anything on my trip. I’d appreciate your humble opinions for this Miss’ippi girl on things not-to-be-missed in Chicago, IL.
This will be the furthest north I’ve ever been, breaking my previous record of South Carolina! 
.:Nichol:.
Go to the Museum of Science and Technology.
Are you a shopper? Madison Ave is fun to walk down and window lick.
Try out the Art Institute - that place is amazing.
Also, Navy Pier is a lot of fun.
The Shedd Aquarium (they have a new shark exhibit!) and the Adler Planetarium.
A previous thread: http://boards.straightdope.com/sdmb/showthread.php?s=&threadid=55798
If you go to the Shedd Aquarium or the Field Museum of Natural History, make sure you go out on the peninsula that leads to the Adler Planetarium and check out the view of the Chicago skyline. You can get a preview from the Adler’s webcam when the fog that’s there at the moment clears.
If you have the time, take a short trip to Indiana Dunes National Lakeshore or Indiana Dunes State Park. There are lots of photos around on Web if you want to see what to expect.
Not to be too nitpicky, but it is called the Museum of Science and Industry, not the Museum of Science and Technology. As for where else to go, try Twin Anchors on North Sedgwick, where you can the best ribs in the world.
Another good place to forage is the Berghof. Don’t miss their bratwurst and beer.
The Berghof has been there since the 1890’s. One of the large museums…either Science and Industry, or Natural History, has a “Chicago in 1900” type exhibit and you can see the Berghoff there, too.
Since no one else has said it yet:
Don’t miss the pizza!! Please send one to Maureen, c/o SDMB. ImissitImissit,IDO! There is no decent pizza on my otherwise wonderful slice of the planet.
Seriously, I did not once have a bad piece of pizza while I was in Chicago (for about 8 months on assignment). Even the stuff at Wrigley Field kicks butt…
which reminds me: See a Cubs game! They now have our beloved Dusty Baker (dammit).
Depends on your interests. Chicago has lots of music and food festivals during the summertime:
Chicago special events calendar
The local PBS station has a show called Wild Chicago that features all kinds of strange and interesting things that are more or less off the beaten path.
Visit the Chicago Reader!
What do you like to do? I probably have a zillion suggestions for you, especially in the realms of music and random ethnic restaurants. Details, man, details!
If you like theater, you must check out *Too Much Light Makes the Baby Go Blind, * at the Neo-Futurarium. You can find the listing in the Reader. 30 plays in 60 minutes, all over the map, with new ones thrown into the mix every week…one minute you’re laughing, the next you’re crying. Fun, but definitely loud, raucous, and not for the faint of heart!
1080 W. Addison. Hopefully I’ll go someday.
Hey, I went there once! There’s a really good Italian restaurant, Volarie, just a short walk from Navy Pier.
Nichol, I hope you enjoy your trip there as much as I did. This country fool got a stiff neck lookin’ up at all the tall concrete. Be sure to see the newspaper buildings after dark with the floodlights on them. They are truly works of art.
Well, I’d say that some improv/ sketch comedy should be seen, since Chicago is the city where the genre was honed. (It’s not an exaggeration to say that SNL probably wouldn’t exist or have survived as long as it has without Second City as an incubator).
Second City is the marquee venue, but obviously is the most tourist-frequented. I haven’t seen the current mainstage show, but the show in the smaller etc. theater has been running since last summer, and was absolutely hilarious last summer. I’m not sure how they’ve modified it since last summer, since some of the jokes that were funny then might be a tad dated now, but I’d recommend that show.
Smaller venues to look at are ImprovOlympic and ComedySportz. The quality of shows at these venues is somewhat more uneven, but often they’re entertaining and much less expensive than Second City.
A Cubs day game is a must. Not a night game. A day game. My fiancee, a die-hard Yankees fan and baseball purist, believes that what the Cubs play is not really baseball. Since I’m not such a purist, I tend to see the Cubs as providing a useful service, namely, getting Loop office workers out of the office early on Friday afternoons. You can also see a Sox game, but U.S. Cellular Field lacks the charm of Wrigley (and by charm, I mean “non-functional bathrooms”).
The Chicago Architecture Foundation sponsors a number of walking and boat tours of the city, which are quite good.
I second the endorsements of the Art Institute, the Field Museum, the Adler Planetarium, the Shedd Aquarium, and the Museum of Science and Industry. I’m more tepid about the Museum of Contemporary Art, though. Maybe it was just from living close to it for five years. But they often have interesting displays out front in the summer, and they do have a Solstice party in June which can be fun.
Neighborhood parties and festivals are also enjoyable. Here’s a list from theMayor’s Office of Special Events.
I’m not a huge fan of Taste of Chicago, but that’s because I live here and have the Taste of Chicago available to me pretty much all the time. If you decide to go, go during the daytime, not the evenings, and stay well clear of the Fourth of July, unless you really enjoy getting crushed by crowds.
I don’t know what your experience of large cities is, but the Magnificient Mile shopping area is a boulevard of big stores that really only draws comparisons with Manhattan. Again, having lived close to it for five years, its charms have worn off for me, but for someone who’s never been to New York, it might be an interesting experience. Just padlock your credit cards.
Outdoor music at Ravinia or Grant Park is a fun diversion.
Tons of stuff, really. Summer in Chicago is the time that almost makes up for the miserable winters.
Take one of the boat rides. I used to catch one on the Chicago River just off the Wrigley building (IIRC). They take you through the city on the river, then out onto Lake Michigan for a while. Nice skyline view from the lake, and IIRC there’s a little lighthouse or something out there too that’s kind of neat. In the summer, I would like to do this to cool off a little bit when walking around the city all day. It’s usually quite cool out on the lake.
Note, this may be of less interest to you if you come from a part of Mississippi where you have convenient access to the gulf, and go boating frequently.
Jeevmon:
Improvolympic is fantastic. And if you come in June, you can see me perform there. 
One of the best nights for newcomers is Wednesday. There is a free evening featuring IO’s signature long-form show, the Harold, which starts at 8PM. If you stick around and you have five bucks in your pocket, at 10:15 or so you can see TJ and Dave, a two person improvised show that never fails to absolutely rock.
Jeevmon is right, the quality is occasionally uneven, but the enthusiasm of the performers and the dizzying highs make up for the occasional moments of mediocrity.
In other news, the park service is bringing back Movies in the Parks, a fun idea that is also cheap. Bring a blanket and a picnic bag and watch a movie under the stars. Sweet.
Shopping is on Michigan Avenue (Magnificent Mile), not Madison Avenue. Madison Avenue is in New York City. But, the Mag Mile is a little tourist trappy - I would suggest venturing out into some of the other Chicago neighborhoods to boutique shop. You can go to Barnes and Noble or Old Navy anywhere. The only store I might suggest going to is American GirlTM Place - http://www.americangirl.com/agpl/ - it’s AMAZING.
Go to the Hancock Building, but instead of taking the elevator all the way up to the observation deck, get off a couple of floors earlier and have a drink (or lunch) at the Signature Room. The fee for the observation deck is around $15.00, you’d spend that or drinks or lunch just as easily. Amazing view.
Definitely catch a Cubs game, an Architectural Tour (walking or by boat). Go to the Lincoln Park Zoo (it’s free!). Try to go to one of the many street festivals during the summer - there is one every weekend.
Go to the theater - there are hundreds of theater companies in Chicago, and sometimes you might get to see a Broadway show before it hits the Old White Way - Chicago is sometimes a run-through town for Broadway productions. http://www.chicagoplays.com/
Here’s a good guide/reviews to restaurants in Chicago - and we have MANY: http://www.networkchicago.com/checkplease/restaurantsatoz.htm. *Check, Please![I/] is a locally produced restaurant review show - any price range/style is mentioned here.
Enjoy!
Another plug for the boat tour. But specifically the architecture tour given by the Chicago Architecture Foundation. The Chicago Tribune rated it the one single thing you can not miss when you visit Chicago.
I have not been on any boat tours given by anyone else, but I plug the CAF tour specifically because it is a non-profit group manned primarily by volunteers (I am one, so if you have any questions about Chicago loop architecture, fire away!)
Pardon my semi-hijack, but:
Are there any new(ish) interesting restaurants in Chicago that are “hot” or “don’t miss”?
The Art Institute it free on Tuesdays. All the major museums have free days, so check the schedules.
There’s some amazing architecture all over the city.
As for food, go to Superdawg in Niles and The Chicago Pizza and Oven Grinder Company on North Clark St.
