Probably the closest thing I've had to an unintentional road trip would be one drive back in mid-March.
It was right as the virus restrictions we're just coming in, so as you can remember, there wasn't really much to do. I set off in my car, southbound from home, with no real destination in mind. I think my primary motivation was going to get food, as it usually is when I want to take a drive somewhere.

Anyways, I kept driving south, then east, and I ended up on the Edens Expressway going south toward Chicago. I kept telling myself I would exit somewhere, since I knew a lot of the fast food in the area. (I went to community college nearby that semester, before we were shut down) But no, I kept going. And going. And, oh look, it's the Kennedy merge.
At that point, I had no interest in food and decided I would drive down to the Chicago Loop for the first time. I'd been downtown before of course, but never driving nor by myself. I got off at Monroe, and just tooled around downtown for a while. Needless to say, it was deserted. And this was before the chaos in May-June, so the city still looked presentable.
After hopping back on north from the Ohio St feeder ramp, I ended up driving myself out to O'Hare, around the departures loop, then back up the Tri-State back home.
This entire trip took just under an hour and a half by the way. Needless to say, this was a very unique opportunity and one I don't think I'll have again.
Here's a picture I got driving away from the airport on I-190.
