I have been planning to make a road trip but not had the time. But 1000 beers sounds great to me! Sergio's has had some financial struggles and growing pains but from what I have seen as of late they seem to behind them. Here is a link
old chicago is a cool place. especially the beer tours. get free stuff in the end. Then there's Ri-ra's at 4th st, the irish bar that was imported from ireland. cool stuff.
bbc downtown is the best. no food but you can bring your own or order from local resturants.
brownings always good
sergio's so many beers to choose from now that everything is prices much easier to decide.
brendans is a good place
old chicago is a good place to get alot of different beers.