heh, I'm doing the old new bike routine too right now. MN here, so similar climate to Chicago. No winter riding, only a little running... have to find an indoor pool that I like. blah.
My current ride is a Trek Y-Foil. Because the frame hasn't been made for a while now, and they are getting more and more rare, I want to cut back the miles on it. So I bought a Klein Q-Pro XX frameset on EBay. Got a sweet price. Will swap my Ultegra stuff from the Trek to the Klein and build that up as my road bike. At the same time the Trek will get new 105 components and a tri/tt specific aerobar setup. I'm going with 105 components because I won't be doing as many miles on that bike, so no need for way more expensive Ultegra or DA parts.