The Shwinn traveler was a decent bike in some years. The Giant Perigee is a sleeper too. Find a bike with 700cm wheels and aero levers in decent shape. Throw in one with decent tires and your a winner.
Not sure about Chicago but the SoCal market always has someone clearing out their garage with a decent early 90's bike that lists it at $125. (That means $100). I'd stay away from flippers. Beat them to a garage sale bike and do a complete relube and maybe new tires on a $100 find. Good luck. Keep us posted.