Taking a quick look at Target's winter coat selection for men... the coats that are appropriate for December - February in Chicago are still in the $150+ range price there. There are some in the $100 that wouldn't be awful for going a block... maybe two... but I wouldn't want to be wearing them if there was a substantial wind, snow, or if I found that I needed to turn around and go back to the bus stop and wait for the next bus.

We're comparing https://www.target.com/p/cutter-buck-mission-ridge-repreve-e... (and honestly, the puffy jackets are... to me, as a local to the upper midwest, those... they're not what you see many locals wearing... some, yes... but not many) to things in https://www.rei.com/c/snow-jackets?ir=category%3Asnow-jacket...