I think if I had the chance to buy a commuter/all around again, I would check out the Surly cross check. It will allow you to put a good range of tire sizes and, for me at least, being in hoods on a road styled bike is more comfortable than a straight bar for commutes or even trail rides. A bit above your price range, but not by much.

http://www.surlybikes.com/bikes/cross_check_complete/

As mentioned, you need to plan for the accessories you need. I would also add that if you plan on riding in upper Illinois in the winter often, you will be going through components like bottom brackets due to corrosion from salt and water damage - so you need to budget that over the long term. I think because of all this ancillary costs you should take the time an try different kinds of bike - hybrids, rood, cyclocross at shops so maybe you can get it right the first time

Good luck.

- Gene