Hello, Chicago: Nice to See You Again

Originally posted on Linkedin August 25, 2026

Being from the Midwest, I've always had a fascination with Chicago.

One of my earliest memories is a family "vacation" organized by my grandparents that took us aboard Amtrak from Holland, Michigan, to Union Station. Granted, we're talking about the late '80s, so aside from distinctly remembering the U-505 submarine and the massive whale skeleton at the Museum of Science and Industry, some of the details are a little cloudy.

But it was my first trip to Chicago, and it certainly wouldn't be my last.

There were school field trips and family trips.

Later came my fascination with aviation and, like so many aviation enthusiasts of my generation, an obsession with Meigs Field and the incredible idea that airplanes could land on the lakefront with the Chicago skyline right outside the window.

Somewhere along the way, Chicago became more than a city I occasionally visited. It became a place that has always felt familiar.

Growing up, my dad always seemed to have WBBM 780 on the radio. As an adult, I continued finding excuses to make the trip myself.

You can ask my daughter how many Saturday mornings started with me waking her up and saying, "Hey, let's go get pizza in Chicago." 

We'd be on our way just minutes later.

For my 40th birthday, I decided I wanted to do something difficult and memorable, so I challenged myself to kayak around Chicago. I launched out of North Ave Beach, watched the sunrise then began my way into the city. Seeing the city from the water, surrounded by its architecture and history, was an experience I'll never forget. 

All of which brings me to why I'm writing this.

VolatusJet is beginning a serious push into the Chicago market.

There are plenty of business reasons for that decision. Chicago is one of America's great centers of commerce and transportation. It sits at the heart of the Midwest and has an extraordinary aviation infrastructure.

But there's also a much simpler reason.

Chicago feels like a second home to me.

And as VolatusJet begins getting to know Chicago professionally, I thought it would be fitting to introduce ourselves by exploring something I've been fascinated by for years: Chicago aviation.

Most people immediately associate flying to Chicago with O'Hare and Midway. Understandably so. But look beyond those two airports and you'll discover an extraordinary network of aviation gateways surrounding the city.

Chicago Executive. DuPage. Waukegan. Aurora. Gary/Chicago. Rockford. Lewis University.

And, historically, the unforgettable Meigs Field.

Each has its own story. Each serves a different piece of the region. Together, they illustrate something I believe is often overlooked when we think about air travel:

Getting to Chicago and getting where you actually need to be in Chicago aren't necessarily the same thing.

So, over the next several weeks, I'll be exploring these airports, their histories, the communities they serve, and some of the stories that have helped Chicago influence not only aviation in the Midwest, but American aviation as a whole.

Some of it will be history. Some will be business aviation. And hopefully, there will be a few things even lifelong Chicagoans didn't know about the airports in their own backyard.

Welcome to:

Chicago Aviation: One City. Many Gateways.

And from VolatusJet—

Hello Chicago, Nice to See You Again.