My wife and I watched this at home as a Netflix streaming movie. I like the "everyman" persona Messina communicates, in 'Giant Mechanical Man' four years ago I wrote about his character "feeling a bit lost in the world and a bit fed up" with his direction. His character in this movie is not too different.
The two main characters are Chris Messina as Kenny Pantalio and Abigail Spencer as Lolita Nowicki. One evening they meet quite by accident, she is on one of the downtown bridges over the Chicago River when he walks up and leans on the railing. The unspoken idea is that he is contemplating suicide. They don't seem to have much in common, and are pretty much opposite personality types, but they walk together. He is still dressed in his day uniform peddling ice cream from his push cart, white pants, white jacket and bow tie.
As they pass a fancy restaurant a man drives up in an expensive car and hands Kenny the keys, mistaking him for the parking valet. As the stranger goes inside Kenny and Lolita (not her real name we later learn) look at each other, again with an unspoken idea, "Let's take this car and get out of here." She suggests San Francisco and after he cogitates for a while decides to be game about it.
So all that happens at the very beginning to set the stage, neither seems to have anything to lose and they set off with little cash and zero preparation. The movie is really about their road trip, the situations they get into and how they get out of them, eventually getting to S.F.
This is a quirky, inventive smaller movie that works just right for Messina and Spencer as the two misfits that band together. In the end, after barely surviving, they just might be able to help each other navigate a better path through life.