Riding the Chicago Skyway

"As I was walking a ribbon of highway I saw above me an endless skyway"

- Woody Guthrie "This Land is Your Land"

This year, with both my kids attending Indiana Universities, I've had the opportunity to make repeated trips along the stretch of tollway known as the Chicago Skyway. The nearly eight mile road was built in 1958, near the end of the Eisenhower administration, which was responsible for building the interstate highway system as we know it today. Before then, the only option for long distance road travel was a patchwork of county roads and smaller highways, the most famous, of course, being Route 66, which ran from Chicago to LA.

So it's fitting, given the era in which it was built, that the Skyway gives off a vibe that reflects that optimistic, Disney Tomorrowland outlook of that period, from the extruded Art Deco block lettering over the entrance to the steel truss bridge spanning the Calumet River.

My first trip on the Skyway was likely at the start of a family vacation, when we made the trip out east for the epic 1964 New York World's Fair. I was too young to remember much about the trip, though I have a vague memory of barfing somewhere along the windy roads of Pennsylvania.

Today, the Skyway entrance looks a bit dingy and dated and the bridge doesn't look quite as majestic as it must have when it was first built. The tollway system, which was supposed to be converted to a freeway system once the roads were paid for, is still around and of course, costlier than ever. The automated i-Pass system, which is supposed to work in tandem with Indiana's i-Zoom system to operate the automated gate with the wave of the magic transponder, frequently has problems, and I'm required to yell the I-Pass number into the tinny 2-way speakers on average once or twice every trip.

I usually make the nine hour roundtrip between Bloomington, IN and Chicago in one day, so by the time I hit the Skyway heading home, it's dark and I'm on my 4th or 5th caffeinated drink. It's just at this point that the tollway splits off into two single lanes flanked by 5-foot-high, shoulderless concrete barriers which weave back and forth. The effect is similar to Luke Skywalker navigating the Death Star trench at the end of Star Wars, and it's always an eye opener no matter what time of day or night. Presumably this is due to some temporary construction rerouting, but it's been this way for years with no sign of a fix.

In the next several years, I expect to make about a dozen or so more trips each way across the Skyway. Maybe a some point during that time, it will be part of that proposed massive infrastructure overhaul that will keep it standing for another millennium or so. Or at least until we finally get those flying cars.