How can I try a wide variety beers without buying them by the case/spending a lot of money? Like most of you here, I thoroughly enjoy beer.
How can I try a wide variety beers without buying them by the case/spending a lot of money? 

Aspiring beer enthusiast that is grows tired of the usual, and wants to branch out.
Also on a broke, paying for school out of pocket, college kid budget.
You can look for breweries in your areas that give tours. These often include free tastings. (Since you mentioned you're from the Chicago area, I know there's a bus tour that takes you to different breweries in Chicago and Milwaukee. There's a fee, but you'd get to try a lot of different beers.)

Also, look for brewpubs and restaurants in your area that sell flights of beer. A flight is 4-5 samples of different beers served together. The cost is normally about the same as a full glass, and the total volume is usually the same or a little more. This allows you to try 4 or 5 different beers for about the same price as you'd normally pay for one.