You聮re a tough guy, Zac. Most Chicago runners head for the treadmills and Stairmasters during winter. But not you. You figure, “I have ten toes, can sacrifice two or three.” The task is to ensure you do not. It聮s a two-part issue聴the shoes, and then the other stuff to keep your feet sort of warm.
The Mountain Masochist GTX听
The shoes part is pretty easy. I聮d go with a sturdy trail-runner, with a Gore-Tex booty. I like the idea of a trail-runner because they have more support when running on icy, crummy streets, probably in the dark.
Take a look at the XA Pro 3D Ultra GTX shoes (a mouthful, for sure). These are really handsome shoes, but very functional, with soles with big knobs for grip, heel and toe caps, Gore XCR booties, and EVA midsoles for cushioning. Just the thing for the mean winter streets ($140).
I also like 聮s Mountain Masochist GTX ($115). Same drill as the Salomons聴grippy soles, Gore-Tex booties (older style, not XCR), toe caps, and EVA midsole. Nice shoes.
I聮d do two things to weatherproof what are essentially low-top sneakers. One, wear woolen socks. PhD Running Light Socks ($16) are a good start. The other thing, wear some gaiters to keep snow/sand/slush out of your shoes. 聮s Flex Tex Gaiters ($35) are mid-height gaiters that are just the ticket for running shoes. They have nylon uppers that repel moisture, and they聮ll add some warmth.
Run on!