If you're going to commute all winter in Chicago you're probably going to want to wear boots. If that's the case then bragi's suggestion comes closest IMO. Don't have to spend that much, though. You can get 9/16" metal BMX pedals with replaceable pins starting at around $25.

I'm running metal BMX pedals with no replacable pins that I got for $5 at a swap meet. When I waste the pins I'll get something with replaceable pins.

I got hooked on BMX pedals when I pulled these off a dumpster score bike. The pins are all rounded off so not so good in the wet, but I've since gotten some fresher ones (at a swap meet for $5) and my feet stick to them like glue.


GT pedals off a dumpster score! by Lester Of Puppets, on Flickr

These freebies were also 1/2", thus the adapters.