I will be stationed in Great Lakes for ten months starting January. I will have very little free time and want to get the best possible Chicago experience. I am looking to put together a list of must see locations. Also would like some suggestions for the best of locations. IE best deep dish pizza, best Chicago dog, best blues bar etc.
There are already threads for most of those categories that you mentioned. The bottom line is that there are no “best of” conclusions. All you’ll get is a lot if things that a lot of people like. Pick any of the suggestions and you really can’t go wrong. Yelp.com is also a great resource, especially if you are looking for establishments near specific locations.
I love such “10 Things you have to do or you have to see” lists. Every time I visit some must see location I can tick it on my list. Yeah this is great.
I’ll nominate Buddy Guy’s Legends for Best Blues Bar, though I’m sure to get some disagreement.
My personal favorite places to visit, in addition to Legends, are the Field Museum and the Art Institute. What can I say: I’m a nerd.
If you like live comedy, Chicago is maybe the best place in the world to see some. The gold standard is Second City’s mainstage revue, but if you stretch out a bit you’ll see some truly great and original stuff, especially in the realm of improv.
iO (formerly ImprovOlympic) on Clark south of Wrigley is a good first step into improv as performance (as opposed to improv as writing tool, which Second City is mostly doing). On Wednesdays at iO there is no cover, drinks are cheap, and the closing team (“Carl and the Passions”) is made up of some of the most talented people in a talented city. Stay until 11PM and pay an extra $5 for TJ and Dave, a show which is always very good and is occasionally transcendent. There are also consistently great themed improv shows there like Improvised Shakespeare and Whirled News Tonight.
iO is a crazy place with dozens of shows every week, the weekends are generally a better bet but you’re probably OK to stop in anytime and check things out.
Even further off the beaten path but even more rewarding when it is good is the Annoyance theater, in a funky, relatively new space on Broadway and putting up well-reviewed stuff all the time (I am less familiar with these guys).
Full disclosure, I am an improv actor in Chicago, have been for a long time. It’s a standard recommendation for me, I find that most people are happy to have tried it at least once, and to me it is one of the things that makes Chicago unique and fun. There’s a lot of crap, but if you stick to well-reviewed shows or find a local who knows the scene you can see some incredible stuff.
Skip the Sears Tower (wait, what’s it called now?) observation deck and go to the Hancock Tower observation deck instead.
If you’re a geek, definitely try to get to the Museum of Science and Industry.
Here are definitely some great suggestions for things you can do when you are in Chicago. I will visit Chicago in summer and will definitely do some things you all have suggested here. I am already looking forward to my visit there.