Bumping for necessity for this to happen.
Most of us are/will be soon on summer break, so we should really get this rolling as dates become more widely available.
Here's just a few ideas of what we can do:
Baseball game (cubs or sox)
Good ol Navy Pier
Dick around at water tower place
Taste of Chicago
Millenium Park
Jerry Springer (We would have to work on this ASAP, for we need to purchase tickets in advance, and its 18+)
Some kind of music festival (Lollapalooza, Bluesfest, etc.)
That's just a couple things we could do, some dependent on dates and such, but ideas nonetheless.