I'm a Chicagoan. A friend of mine from high school is big into long haul EV trips (in his Tesla); every couple of weeks I get a trip report. It never seems to be as simple as you're making it out to be; he always seems to hit pretty substantial charging delays. Nothing that makes the trips untenable --- he's sold on it. But it's not like "charging just fits into what you'd normally do at a rest stop".