On travel medical insurance

One of the guys I work with is going back home to Bulgaria for a 2-week visit. Maybe he has some business to do there. Or maybe it's just personal. I don't know. He's driving today to Chicago where his brother lives. He'll be able to park his car at his brother's house, then take a flight to Rome, then change flights to Bulgaria. I guess there aren't any direct flights to there from America, which makes sense. We talked about how I thought it'd be cheaper to fly from St Louis to Chicago, but I was thinking about the expense of leaving my car at the airport in Chicago if I drove there. He doesn't have that problem. He's young and healthy so I doubt if he is taking out any travel medical insurance.