I'm sure I'll repeat a lot, but having lived there:
Touristy Things:
-Bean is actually cool Yes
-Hancock > Sears, agreed Yes
-Field Museum, Art Museum, and Shedd are all cool, I'd say art museum is best Yes
-Second City is a must Yes
Places to Eat
-Billy Goat Tavern No
-Weiner Circle Would recommend Hot Dougs first, but Weiner Circle is good.
-House of Blues has good food and is great to check out, better if you can see a show there
-Lots of other streetside joints that are awesome
Bars, tons in town to go to but personal favorites
-Hangge Uppe (don't get there until 11pm and plan on staying all night) Oh God NO. This place is the equivalent of an Ames dance bar (tazzles, dean's list, sips, paddy's, or whatever these places are called today)
-Zebra Lounge (piano bar but less of a mess than the touristy bars) Yes
-Lincoln Park and Wrigleyville have great places but are better when Cubs are playing
Music Venues (if you can see a show) all good places
-Aragon Ballroom
-The Metro
-Double Door
-Vic/Riv/Chicago Theatre are all awesome
Other things:
-Lots of great record stores in town
-Beaches are fun in the summer, some have bars as well yes
-If you can rent bikes, a ride along the lake shore will be a ton of fun and you can see a lot of things easily. Watching old dudes play speed chess in Lincoln Park is awesome The bike rental is fun, but at your own risk, as bike riding along the lake can get pretty hairy in spots