Just had this info sent to me:
Things that are fun:
Rush street-tons of bars, lots of night life. Don’t stray too far off the beaten path, some the neighborhoods around there are pretty scary
Museum of Science and Industry and the Field Museum are GREAT. I haven’t been there in years but always enjoyed it as a kid
Buckingham fountain-it may be done for the year but they used to have a really fun light/music/fountain show each night
Ride the EL
LOTS of Blues Bars, they even have a Blues fest but I can’t remember when it is
Go to the top of the Sears tower, it is particularly fun when it is really windy and you can feel the building sway
Navy Pier-permanent carnival type thing
Concerts all the time
There are lots of forest preserves and green spaces all over the place to hike