I've driven from Madison, WI to Chicago in an EV with ~100 mile range in cold weather. Wouldn't be my first choice, but I was in a pinch at the time. It can work, but getting a reliable charger network is the biggest problem. Made three stops to chargers that were broken or inaccessible for various reasons.

That was a couple of years back, and I think it'd go a bit smoother now. The Chicagoland area has reasonably good charger network outlays (much better than Minneapolis, which is a joke). Still wouldn't be my first choice, but it's workable.