Where do you like to meet up for local buy/sell exchanges in winter?

Meeting a stranger to swap a couch or a used bike is a little trickier once it's dark by late afternoon and the sidewalks get icy. Many people suggest well-lit public places, but it would be great to hear what actually works in your neighborhood.

Do you have go-to safe meetup spots in Chicago or the suburbs, any tips for handling bigger items when the weather turns, or lessons learned from past exchanges? What advice would you give someone making their first local sale this season?