Look for something used on craigslist. You can definitely find some good used stuff. Plus, riding around on a vintage machine is so much more classy than riding on some lame hybrid/commutermobile that 40-year-old Larry rides from his house to the office everyday. You need something swank, and you're not going to find that for $300 in the new bike world.
Look at these two smart bikes in the MPLS area:
Schwinn continental - bronze and neon green
Fuji single speed - Gray and neon yellow
There is simply no way that you will be able to find a new bike with either a pink chain, or neon green or yellow bar tape, and you know that, with a combination of style, functionality and pinache like that, there is no way you can go wrong.