Heh, Rival pretty much has it right for what to do in Bloomington.
On the bright side though, you're less than an hour from Indianapolis. I've only spent one night in Indianapolis so other than the Indy500 track, I won't be much help there.
Hmm, there is a big casino down in Evansville if you are into gambling.
On the other side Chicago is 3 - 4 hours away. There are museums galore there, an aquarium, navy pier, sears tower. As for eats you of course have to hit Gino's East for some of the worlds best pizza.
My advice is spend your days off in Chicago, and your evenings in Indianapolis.
Here is one link I found quickly for
Chicago.
You can probably find tons of em on the web though.