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Travel New York To Chicago

Highway travel in the USA.

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ROCHESTER, New York- Our Great American Road Trip began with a great fight with my wife. So far, so typical — what long journey doesn’t start out this way?

It was a nothing kind of fight. By the time we were in the car we’d both forgotten what it was even about. The sun was shining and the sky was blue. It was a perfect July morning — like the kind you imagine from reading a turn of the century era classic novel about the US countryside. Everything just kind of has this golden tinge.

I have nothing to report on from Rochester to Chicago. There was a road, there were cars, there were rest stops.

There were also self-operated toll booths.

These seem like a good idea — why pay to have someone sit in a box collecting money when a machine could do it cheaper? — until you sit in a long line for ten to twenty minutes behind someone who doesn’t understand how to work the machine.

Technological ignorance is perhaps the greatest logistical bottleneck in the USA, and is one of the reasons why populations in emerging markets are starting to pass us by. This is a country of people who think they don’t need to adapt, that they can keep doing things as they’ve always done it and the world will change for them. You can go far, far out into the hills of China to a remote village of subsistence farmers and find these old people who can use their smartphones better than half the USA. They learn and adapt because they know they don’t have a choice. We think we have a choice and this is one of the worst — and perhaps best — aspects of America.

But this was not my primary concern when I sat in that line of cars waiting for someone who couldn’t work the electronic toll machine. The ever-growing line of cars leading down the ramp and back onto the highway was a far greater problem. This shit show was crossing the divide from inconvenient to dangerous.

I opened my door and leapt out. My wife squealed, “Where are you going!?!” I ran down the row of cars to the front of the line. Some old guy was all flustered and confused, impotently trying to stuff his dollar into the machine for what was probably the five hundredth time to no avail.

“Of course, a f’cking geezer,” I thought. I snatched the guy’s dollar and tried to shove it in the slot.

The bill slot was switched off. No joke. The light on the machine was off and it wasn’t accepting any bills. I tried to swipe my debit card for him. At this point he was too discombobulated to function and it wasn’t worth asking him for his card — I’d spare $1.35 to get this situation done. It didn’t work either.

The machine had malfunctioned or was switched off. I looked back at the line of cars piling up. There was a gate in the downward position in front of the geezer’s car. The poor guy was trapped. There was nowhere for anybody to go. I found a dirt obscured help button and pushed it.

“Uh, that machine is only taking coins,” the voice said.

“What if someone doesn’t have enough change on them?” I had to ask.

And I thought humans sitting in booths collecting tolls by hand was archaic.

Anyway, I guess we’re trying to phase cash out entirely, making cash inconvenient in an attempt to get us onto the fully digital grid where all of our purchases, preferences, locations, and movements are logged and tracked. Cash will be criminal, and a wad of it will in and of itself be cause for suspicion — what drugs are you dealing, cash man?

Soon enough cash will be phased out. Convenience and public safety will be the stated reasons. We will shrug, use our cards, and live on the grid. It’s almost to that point already. When was the last time I went inside at a gas station to pay with cash?

I guess I should appreciate the fact that I can still use cash in the USA. China is already approaching a cashless state, India recently culled most its banknotes to force financial digitalization, and in more and more places paper money is become a novel and almost comical sight.

We are traveling into a new era and the use of cash is becoming an act of rebellion or some sort of odd preemptive nostalgia.

We’re stopping in Chicago because my wife has a high-school friend there. She became immensely successful in recent years, rising up to the pinnacle of the city’s culinary scene with a bakery that has pretty much become famous — it’s featured in all kinds of movies and shows and commercials.

She bought a house in the west of Chicago, and as we pulled off the highway we didn’t really know what to expect. I’m not sure if I’ve seen anything like this before: rough, broken down ghetto areas were interspersed with nice, wealthy looking areas. It was like demographic stripes. I couldn’t tell if I was looking at urban decay or gentrification or both?

My wife’s friend lived in a ghetto-y section. People stuck their heads out of car windows and screamed at us as we drove. There was around twenty kids playing in a blow up swimming pool on a sidewalk. The corner liquor store was surrounded by an immovable mob.

We parked in front of her house and I said hello to the old black guy watching me from his porch next door. He smiled and returned the greeting. The street was quiet. Three doors away was a crack house but across the street from it was a well kept home and many of the cars parked on the street were rather nice. A teenager drove a dirt bike up and down the sidewalk. The place seemed lawless but well-run and friendly. There were eyeballs everywhere — people hanging out in the streets, on porches, behind open doorways — watching everything.

“This is statistically one of the worst parts of Chicago,” my wife’s friend’s husband said. “But look out there. It doesn’t seem that bad to me.”

This is the face of the new American city, hovering somewhere between really nice and really not nice. But I’d feel safer living here than in some sterile suburb where nobody knows, watches out for, or gives a shit about their neighbor. Those are the scary places.


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Filed under: Illinois, Road Trip

About the Author:

I am the founder and editor of Vagabond Journey. I’ve been traveling the world since 1999, through 91 countries. I am the author of the book, Ghost Cities of China and have written for The Guardian, Forbes, Bloomberg, The Diplomat, the South China Morning Post, and other publications. has written 3715 posts on Vagabond Journey. Contact the author.

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VBJ is currently in: New York City

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