Life on the CTA: Small Moments of Humanity on Chicago’s Trains

Observations from years spent riding Chicago’s CTA trains — moments of humor, grief, connection, conflict, music, and humanity unfolding between strangers.

Years ago, I realized how much wisdom could be found on train rides — or maybe hundreds of train rides — if you actually paid attention.

The following are small moments and observations gathered from years of riding Chicago’s CTA trains. Some are humorous, some sad, some strangely profound, but all of them are real.

Sometimes life happens while we’re simply traveling from one place to another.

Sometimes all we have to do is pay attention.

Green Line

An older man in his sixties sat on the train blasting Waiting for a Girl Like You by Foreigner from his phone, followed immediately by Boston’s More Than a Feeling.

Passengers looked irritated and confused. But somewhere halfway through the Foreigner song, something strange happened.

People throughout the train — different ages, races, and backgrounds — slowly started mouthing the lyrics under their breath. By the time Boston came on, several people were quietly humming along together.

One woman gently swayed to the music while trying not to make it obvious.

For a few minutes, strangers became connected through shared memory and music.

And honestly, I realized music really can bring people together in unexpected ways.

Especially on the Green Line through the west side of Chicago.

Apparently even through Foreigner.

Brown Line

Not long after getting married, I ran into an old friend from recovery while riding the Brown Line.

He told me his life was finally improving — he was sober, getting married, and moving out of state. Months later, I ran into him again after he relapsed and returned to Chicago.

Over the years, we kept unexpectedly crossing paths on trains.

Sometimes he was doing well.
Sometimes he was struggling deeply.

Each encounter felt like a snapshot of someone trying to hold their life together while still searching for meaning, direction, and stability.

In 2016, he died from a drug overdose.

I still think about those train encounters often.

Under different circumstances, maybe we would have become closer friends. But instead, we became two people repeatedly reconnecting in passing moments on the Brown Line through Old Town, Lincoln Park, and Uptown.

Two ships passing in the night.

Blue Line

A disheveled man began blasting Ja Rule and J.Lo’s I’m Real through his phone speakers while riding the Blue Line.

Eventually, another passenger became furious.

Not because the music was loud — but because it was Ja Rule.

For several minutes, the angry passenger passionately criticized Ja Rule’s music, lyrics, and inability to carry ballads.

Surprisingly, the man blasting the music listened carefully.

Then he quietly muted the song.

The two men nodded at each other respectfully, almost like they had reached some strange form of emotional understanding.

Honestly, it felt oddly beautiful.

Red Line

One afternoon, a man politely asked passengers for spare change while holding an empty Starbucks cup.

Another passenger loudly mocked him for using a Starbucks cup while asking for money.

I remember wondering why people automatically assume the worst about strangers who are struggling.

I didn’t have cash to give him, but I offered him a piece of gum instead.

At first he looked confused, maybe even slightly offended.

Then he accepted it.

We stood there chewing gum together in silence before he got off at the next stop.

“Thanks bruh,” he said before leaving.

Small moments matter more than we realize.

Green Line

Two older women discussed politics and city violence while a teenage girl boarded the train blasting music loudly from a portable speaker.

She repeatedly asked everyone if the music bothered them, almost daring someone to react.

Eventually, one of the women politely asked her to lower the volume.

The girl paused, looked down, and quietly turned it off.

And I remember thinking:
Maybe she just wanted someone to speak to her respectfully.

Maybe all of us do.

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