We should start a glove thread for people who exclusively live in Chicago or the Upper Midwest. I’ve spent a small fortune trying to get the right gloves and glove layers over the years.
Every time I start a conversation about cycling gloves and realize I’m talking to a rider from the U.K. I immediately discredit everything they’ve said 
(I say that tongue-in-cheek) — I mean, there is winter, and then there is WINTER 
Also, here’s a plug for my favorite piece of shoulder season riding gear:
The roadie inside you will reject it. The gravel grinder inside you will say it’s too small. But it holds a rolled up windvest, an pair of liner gloves and a headband absolutely perfectly. I hate having clothes in my back pocket. Maybe that’s just me.