Chicago Aviation: One City. Many Gateways Part 2: The Dirt Strip That Built an Industry: The Real Story of Chicago Executive

Originally posted on LinkedIn September 8, 2026

If you grew up listening to WBBM on the radio or flying regional routes around Chicago, you probably didn’t call it Chicago Executive Airport.

You called it Palwaukee.

And Palwaukee wasn’t some carefully chosen aviation brand. The name came from exactly where the airport was located: near the intersection of Palatine Road and Milwaukee Avenue.

The airport itself dates back to 1926, when it was little more than 40 acres of grass and a cinder landing strip. It started as Gauthier’s Flying Field, later became Swallow Airplane Field—named for a Swallow OX-5 based there—and by November 1928 had formally incorporated as Pal-Waukee Air Port.

It’s hard to picture now, especially if your image of PWK is Gulfstreams and Challengers sitting on the ramp, but this was a very different place in those days.

By the 1930s, the airport had grown to 91 acres. During Chicago’s 1933 Century of Progress World’s Fair, a large hangar was built to house the Goodyear Blimp, which carried passengers on sightseeing flights over Chicago and Lake Michigan. World War II brought more activity and expansion, and the airport eventually grew to 109 acres with a gravel runway and dozens of T-hangars.

Then came the part of the story that really shaped the PWK we know today.

In 1953, Priester Aviation acquired the airport.

George Priester was a former Chicago & North Western locomotive engineer who had fallen in love with flying. More importantly, he understood something about aviation that would become increasingly obvious over the next several decades: airplanes weren't only recreational machines. For businesses, they could be working tools.

That idea helped change Palwaukee.

George and later his son Charlie spent the next several decades building an airport capable of handling the kind of corporate aviation that was beginning to emerge. Runway lighting went in. Corporate hangars were built. Navigation and instrument capabilities improved. Eventually, Palwaukee had a 5,000-foot primary runway.

The FAA commissioned an air traffic control tower there in 1967, followed by an Instrument Landing System in 1974. By the early 1980s, Palwaukee had become one of the busiest privately owned airports in the world.

That success also created a problem: land this close to Chicago was becoming far too valuable to assume it would remain an airport forever.

So in 1986, Prospect Heights and Wheeling stepped in. The two municipalities jointly purchased Palwaukee, using a combination of federal and state grants and airport-generated revenue. The airport survived, and twenty years later—on October 17, 2006—it officially became Chicago Executive Airport.

PWK today looks almost nothing like that 40-acre grass field from 1926.

The airport covers more than 400 acres, has three runways, operates around the clock and is home to hundreds of aircraft. But the reason it matters to business aviation is actually pretty simple:

Look at where it is.

PWK sits roughly 10 miles north of O’Hare, with the North Shore on one side and the corporate centers of Cook and Lake Counties surrounding it.

That can make a tremendous difference when the airplane is only one part of the trip.

Flying a business team through O’Hare can mean airline schedules, terminal congestion, long taxi times and then the process of getting everyone out of one of the busiest airports in the country.

At PWK, you can land, taxi to the FBO, get into a waiting car and be on your way.

And that's really the point.

The value of business aviation isn't simply getting an airplane into Chicago-area airspace. It's getting the people on that airplane where they actually need to be.

Nearly a century after someone carved a landing strip into a patch of grass near Palatine Road and Milwaukee Avenue, Palwaukee is still doing exactly that.

And for a lot of people around Chicago, no matter what the sign out front says, it will probably always be Palwaukee.