Chicago to NYC: Notes from the Rails

“How do you possibly endure these journeys?” Family, friends and others keep circling back to the same question.

Ten-hour overnight coaches across Turkey. Greyhounds on the U.S. West Coast and across Texas.

And now, twenty-five hours of steel and scenery from Chicago’s Union Station to New York’s Penn Station.

“I would take the train every time.” My short answer.

Airports have long lost their allure. Domestic U.S. air travel is misery disguised as security: endless ID checks, fingerprint scans, facial recognition, shoes and belts stripped off, dignity reduced to whatever the conveyor belt spits out. You don’t fly, you flee. Amtrak felt different. No one asked for documents or biometrics. I could step off at Cleveland, grab a snack, stretch, and hop back on without fear of being flagged as an outsider. For once, travel felt like belonging.

That sense of contrast sharpened when I thought back to Greyhound. I had done my share of long rides there too - up the West Coast and across Texas. Those trips were endurance of another kind. Terminals that smelled of urine and weed, carrying the uneasy weight of homelessness. Coaches that were cramped, dirty, and often unsafe. The lesson of surrender and patience was present there too, but the tone was different. Greyhound demanded survival. Amtrak offered community.

This train was not just transport. It was a moving neighborhood. Families wrestling with strollers. College kids half-asleep with headphones. Retirees greeting conductors like old friends. Cabin staff who moved through the cars with familiarity rather than authority. I wasn’t anonymous. I was stitched in.

The perks were practical but meaningful. More legroom than any flight. The freedom to wander. Surprisingly excellent 5G that allowed me to watch Netflix, answer emails, draft documents, even tinker with PowerPoint slides. Reflecting on Rumi, Nietzsche, and quarterly Key Performance Indicators (KPIs) or work-related metrics all in one carriage was oddly nostalgic. It pulled me back to my journey to Konya in Turkiye, where Heech at Shams’ tomb had once given new meaning to emptiness [a story I explored here].

Of course, there were absurdities too: bitter coffee, a dining car menu that redefined processed, and bathroom queues that tested patience in new ways. But even those annoyances folded back into the rhythm of the journey.

The truth is that long rides - whether by coach or by rail - have always been spiritual for me. Endurance, patience, quiet, tolerance. The steady hum of wheels becomes meditation. Watching farmland, rivers, and industrial edges slip past, I found myself not waiting for New York, but already arriving in each passing moment. On the train, time stretched instead of shrinking. It no longer felt like something I was chasing or wishing away, but something I was inside of, unhurried. Silence was not empty. It listened back.

“Design is storytelling.” I remind myself of this often, but here it unfolded without effort. The train was designed not in sleek blueprints but in lived choreography: people, space, and time moving together. The ride became its own safar, an outward journey mirroring one inward. Sufis have always known that the road teaches more than the destination. Patience when the train slowed. Tolerance when the bathroom line grew long. Humility when the Wi-Fi blinked out mid-sentence.

Amtrak’s design is imperfect, but it is human. No sterile checkpoints. No biometric suspicion. Space to stretch, aisles to walk, the freedom to step off, smoke, and back on without penalty. Features that quietly signal dignity and trust. The story the train tells is simple: you belong. Not as a passenger number, but as a fellow traveler. And that is what turns endurance into insight, and motion into meaning.

When Penn Station finally appeared, I realized the real arrival had already happened. Somewhere between emails and daydreams, landscapes, waterscapes, airscapes, and overheard conversations, I had reached what I came for: reflection in motion, belonging without pretense.

And yet, the story didn’t end at Penn Station. My farewell to the U.S. was not the quiet stretch of legs on an Amtrak platform but the chaos of a fifteen-hour flight out of JFK. Crowds funneled into queues, shoes off again, liquids scrutinized, laptops shuffled, humanity compressed into metal tubes.

Whatever I had gained in patience and perspective through train travel was tested in the security line, delayed while TSA agents debated over the kinds of questionable items people insist on carrying in hand luggage - stories for another day.

The point is simple: journeys rarely resolve neatly. They just keep stretching, folding, and amusing in unexpected ways.

from Rambling of an Itinerant

Reference. Mian A. Fragments from a Pilgrimage: Rumi, Shams, and the Rest of Us.

In acknowledgment: Co-piloted with GenAI, nudged by memorable travel, and much gratitude.