Airport Portraits: A Satirical AI Take on Travel Art

BY MARK CHESNUT

The airport is where time collapses. Where people wait more than they move. Where signage speaks louder than emotion. That’s the takeoff point for Airport Portraits, my new series of offbeat travel images that depict a satirical and stylized world, built from the blandest aspects of air travel and the weirder corners of my imagination.

This is far from the usual, predictable “travel art” you usually find online.

As part of my new Transglobal Gallery project, Airport Portraits is a retro-inspired, AI-assisted exploration of the joys, frustrations and surreal rituals of travel. It's a fictional universe built to look like the real one — if it had been art-directed by the Department of Transportation in 1974 and emotionally choreographed by a particularly cynical flight attendant who had a thing for Wes Anderson.

All of these images were created using generative AI tools, but every detail — from the eyeshadow to the rotary phones — was directed, curated and styled by me. This is what happens when you take years of experience as a travel writer borne of a childhood obsession with the airline industry, and push it all through a mid-century aesthetic filter, enhanced by the banal emotions that color airport life.

The world of Airport Portraits unfolds inside a bland, unnamed airport — the kind with too much taupe and not enough jet-set glamour. Its flagship airline is the perhaps inappropriately named Happy Skies, a fictional midwestern carrier whose name implies more joy than the faces of its employees ever convey. In fact, joy seems to have caught a flight that’s already departed from this beige airfield. Instead, you'll find stoicism, exhaustion and perhaps a bit of existential dread — all rendered in perfect symmetry and a color palette borrowed from an airline upholstery catalog circa 1973.

In this collection, a rental car agent clutches an empty gas can outside "Can’t Miss Car Rentals." An immigration officer grasps a passport in front of falling signage. A weary couple in the Tranquility Lounge sits motionless, him with a martini and a donut, her on a phone call with someone we’ll likely never know.

Then there are the flight attendants. One slurps a single strand of spaghetti in the Airport Coffee Shop. Another holds an airsickness bag with the resigned gravitas of a hostage negotiator, probably in preparation for any incidents with the nearby baby who’s about to board. A gate agent, meanwhile, inexplicably torches a boarding pass under a sign that reads, simply, Happy Skies.

The Happy Skies brand looms large across the collection. It’s both an airline and a state of emotional contradiction. Its slogan, "The Airline That Smiles Back," rings hollow in an image promoting "exquisite 2-stop HappyJet service" from Peoria to Marion/Herrin, Illinois. The ad features a deadpan woman in sunglasses clutching a drink that’s festive in color only.

Another image spotlights "Mr. Happy Skies," a muscular man in a sash — apparently celebrating his win in some strange airline beauty pageant by flexing on the tarmac, while the stewardess beside him gazes off with all the enthusiasm of a DMV renewal clerk. There's also Carol, a gate agent preparing to board a flight headed to Paducah and Cape Girardeau, sharing her workspace with a baby in a bonnet and a cigarette that seems to be the only thing keeping her tethered to this dimension.

The interiors are clean, beige, and symmetrical — settings where nothing really happens except waiting. Every phone is rotary. Every smile is missing. And yet, it’s all so eerily beautiful.

These images are AI-generated, yes. But they are not AI-directed. Every image is the result of careful creative input, relentless refinement and a healthy sense of irony. My years as a travel writer have taught me not just where to look, but how. And in this case, that "how" means looking beyond the physical trappings of travel. Because travel is really about people. About emotions — or lack thereof. The airport is an absurd theater, at times. A place where everyone is performing, everyone is waiting, and no one’s quite sure where they are emotionally.

Airport Portraits demonstrates how generative AI, when guided by a curious and creative human mind, can go beyond mimicry and become a legitimate tool for conceptual storytelling. This isn’t just about playing with tools. It’s about building new ways to observe and critique a world we thought we understood—and doing it with just enough retro flair and nostalgia to keep you entertained and maybe spark some memories.

I’ve spent decades immersed in and obsessed with the world of travel — from the early days jetting Ozark Air Lines with my mother and stealing things from airports (more in my memoir, Prepare for Departure) to my grown-up career writing about destinations, airlines, hotels and the people who move through them. Airport Portraits is just one more manifestation of my fascination with travel — this time in the form of a satirical, visual love letter to the industry. It captures both my affection for and disillusionment with travel culture. It also represents my first step into what I hope will be a broader exploration of AI-assisted travel art and creativity.

Airport Portraits exists because I love travel. I love airports. And because I think nostalgia is more interesting when it has emotional baggage — and exists just one concourse over from reality.

In the end, Airport Portraits isn't just about the past. It's also about how the past continues to shape how we see the present — and about what's possible when technology is used not to replace creativity, but to amplify it. AI is my co-pilot here, but I’m still flying the plane, baby, and I’m serving the drinks (at least in the first-class cabin).

So whether you're a travel addict, an airline employee or just someone who’s stared at strange-looking people at Gate C17, this series is for you. Welcome aboard.

Are you intrigued by, fascinated with or repulsed by this new wave of travel art and imagery? Well, then, don’t stop now. You can explore more of my travel-inspired art in the Transglobal Gallery, my online home for creative AI travel art projects. In this Instagram account, you'll find a variety of imaginative works in addition to Airport Portraits — in styles that range from Mexican muralist to cubist and surreal, all grounded in my decades-long fascination with the culture of travel.

Some of these works are also available as prints and merchandise in my Redbubble shop. Through these platforms, I'm excited to share a fresh — albeit retro-inspired and bizarre — visual take on how we move through the world.

Please — let me know what you think about these creations, and what you'd like to see more of! 

ABOUT MARK CHESNUT

Mark Chesnut is a New York City-based journalist, editor, travel industry consultant and public speaker with more than 30 years of experience. The winner of the 2019 NLGJA Excellence in Travel Writing Award, Mark is the author of the book Prepare for Departure. Follow him on Instagram!