Right after I graduated I moved back to my hometown (Medina, Cleveland/Akron suburb) and worked in Auditing. As such I usually worked at client sites rather than the main office. I didn't have GPS back then so I printed mapquest directions. I only ever used them the first time, after that I just knew. Honestly, if you asked me today (20+ years later) to drive to one of those, I'd have no problem doing it. Conversely, there are places I have been many, many times with GPS that I still don't actually know the route because instead of looking for streets I've just turned when the lady in the box on my dash (later in my dash) told me to turn.
My second example relates to CFB and is similar to your "lost in Chicago" story. So my brother and I went to the 2001 Ohio State at Michigan football game, pre-GPS. Ann Arbor is almost as bad as State College in terms of GameDay traffic because both are small cities that would more-or-less disappear if you removed the University.
I take pride in the fact that I still learn how to get places and once I've been there (sometimes once, sometimes it takes a few) I can navigate just fine w/o GPS. I used to have to travel to Colorado frequently for work, and if I could get through an entire trip, seeing multiple customers, w/o GPS I was happy.
I've told this story before, but per your football story I have to recount the 2001 Rose Bowl. I moved to CA literally that week. As in arrived in San Jose, dropped all my stuff in a storage unit b/c I couldn't get into my apartment for another week, and then drove down the 101 to meet up with buddies for the game. I think I had bought a CA map (that didn't show anything more detailed than major highways), didn't have a cellphone, and had never been to SoCal and was meeting people who had never been to SoCal.
I managed to drive down there, locate my buddies based on calling (from a payphone) the one person in the group who had a cellphone, and found them off Wilshire Blvd in LA.
I don't think anyone under the age of 35 could accomplish this today lol ;-)