Thumbing it Mafia Style – Chicago, Illinois, USA

I was working for a U.S. airline and taking full advantage of the free flight benefits the employees were offered. For my first trip, I decided to head north to visit my family in Chicago and escape the oppressive heat of Phoenix in August. As will often happen when flying standby, the direct flights were a over-sold and that made creativity the name of the game. In a situation like this, it’s a race to beat the other standby passengers to the next best options; I bolted over to the departure listing screen and decided what the next closest city was with the next available flight. Getting bumped off of a flight always makes the whole experience more of a crazy adventure. With the right attitude, it can end up being the best part of the trip.

Milwaukee was the best alternative for getting to Chicago; I jumped on the next flight out and decided to figure out the rest of the logistics after landing. Finding yourself in a strange, new airport, totally lost and without transportation, can be a bit disconcerting, but a backpacker's life comes at you fast. You might lose your passport and be stranded, or you might get off at the wrong bus stop; either way you learn to improvise. The flight landed around eleven-thirty at night and, as fate would have it, all buses had stopped running for the night.

Options at times like this are always slim. In this case they were: sleep in the airport to wait for the morning bus, call a shuttle service, rent a car, or try to hitch it. Sleeping in airports is an old pastime of mine and one I enjoy, but I was energized, so I decided to give hitching a go before resorting to shoveling out a ridiculous amount of cash for a two-hour ride. I boldly walked into the car rental area and asked for a show of hands on who was going to Chicago. Two business men in front of me, dressed in nice Italian suits, hesitantly raised their hands.

“Where you guys headed?"


“Can I bum a ride?”

“Uh… Sure. You’re gonna pay the tolls.”


John and Steve had flown out of O’Hare to Newark earlier that morning and had almost gotten stuck there after their flight back had been cancelled. Like me, they thought of rerouting through Milwaukee.

“So what were you guys doing in Jersey today?” I probed innocently from the back seat of the premium full-size rental car.

“A little business down by the docks,” came the paused response from John, the driver. “Ok…” I replied, fully amused with the possibilities. “What kind of business do ya’ll do?”

Silence emanated from the front of the car.

“Uh, Jake, What about you’s? What do you do? What brings you to Chicago?” Steve asked, changing the subject. I told the guys about my job, where I was from and about my travels. Then, being the inquisitive idiot, I again posed a question: “Were you guys filling cement shoes in Jersey or something?”

More silence. “Jake, be glad you’re not riding in the trunk.”

I laughed as I answered my cell. It was my mother calling to check on me. I made it a point to not tell my parents about hitching adventures until after they were over. This time though, I went with the straight approach.

“Hey Mom! No, I’m fine. I hitched a ride with these two mafia guys who just finished doing a lil business down on the docks in Jersey, if you know what I mean,” I said, trying my best Italian mafia voice. I got a scowl from Steve in the front; he told me to stop scaring my mother. “Listen Mom, I’m gravy. I’ll call you from Grandpa’s.”

We go back to talking about the weather and other inconsequential things when finally John confessed: “Aight, listen. We’s pro fishermen. We had a tournament in Jersey today.” I turned this over in my head, realizing they only had two small day bags. “Where’s your gear? Your poles and whatnot?” Once again, nothing but silence from the front seat. Steve started laughing ominously and asked if I’ll ever hitch again after this.

We pulled into O’Hare’s rental return. I somehow managed to get out of being fitted for concrete shoes and tossed off a bridge. The mafia guys made sure I had a ride the rest of the way to my grandparents before they headed off.

My love affair with thumbing rides comes down to the mystery of what awaits inside the stranger’s car. It is an exhilarating experience to find oneself in some of the situations hitching provides. At the end of the day, you learn who you share the road with everyday, people we would otherwise ignore from inside our own air-conditioned box on wheels.

That’s what the world really needs, isn’t it? Just a few more people willing to open their doors and hearts to the strangers who surround them.

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