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The Chicago Skyway was for years a financial albatross

Who would buy something that doesn’t look like a bridge, doesn’t act like a bridge, but is offered for sale as a bridge? That is what Atlas Arteria recently did. The Australian company spent $2 billion to acquire a 67% interest in the Chicago Skyway.

The word “bridge” suggests a structure that passes over a river or a lake. Perhaps railroad tracks. But for most of its 7.8 miles, the Chicago Skyway, officially a toll bridge, just hovers over cross streets that were buried in its path.

Stretching between the Dan Ryan Expressway and the Illinois-Indiana border, the Skyway has an effect similar to that of the Berlin Wall, which separated East and West Germany, in how it slices up Chicago’s Southeast Side. Looking up at it from the streets below, the mind conjures a preteen Romeo living in the 7400 block of South Greenwood Avenue, cut off by the towering expressway from a Juliet in the 7500 block. Could their schoolyard romance survive the Skyway?

In 1966, Donald Bonniwell, a state highway commissioner, decried the Chicago Skyway as “a concrete curtain cutting off access by people in the southeast section of the city.”

Its construction was the result of a spitball Indiana threw at Chicago in 1953.

The Cold War was on, prompting the building of intercity superhighways so urbanites could be evacuated if atomic warfare threatened. Illinois planners assumed that Indiana’s expressway network would join their state’s network south of Chicago, thus avoiding the congestion of a metropolis.

Then Indiana announced it was building a toll road straight across the state from Ohio that would end abruptly at Chicago’s border, at 106th Street and Indianapolis Boulevard.

“Indiana has been selfish in its planning,” Ald. Emil Pacini of the 10th Ward, which included that intersection, protested to the Tribune.

Pacini’s ward and adjacent neighborhoods were patchwork quilts of industrial plants and streets lined with the homes of workers. A subdivision of the neighboring South Chicago community was known as “The Bush” because the houses were so densely packed they resembled shrubbery.

“The new superhighway would dump at least 18,000 cars a day into Chicago at a place that can’t handle the traffic properly now,” Pacini told his City Council colleagues.

It seemed clear that the Southeast Side needed a superhighway to disperse the traffic that Indiana would send Chicago’s way. But Republicans who controlled the Illinois Toll Highway Commission refused to pay for a superhighway connection to the Indiana Toll Road. Chicago then as now was a Democratic stronghold, and the GOP wasn’t about to bail it out.

So Chicago had to fund a connecting road. Under Illinois law, the city was prohibited from operating a toll road. But it could put up a toll bridge, a legal distinction that allowed construction of the skyway to move forward.

The Skyway had to cross the Calumet River on its way toward the Illinois-Indiana border. That portion was built with spans of steel plates supported by structural-steel trusses, and the result looks like a picture-book bridge. Any bridge needs an entrance ramp, and the Skyway’s is wondrously formidable: an embankment stretching from the Calumet’s western bank to State Street at 66th Street, where it joins the Dan Ryan.

The Skyway’s construction was a tragedy for many of those living or running a business along its route. In 1957, Adeline Field, a retired phone operator, came to her door at 6815 Anthony Ave. with a shotgun in her hand. All the other buildings on the block had been torn down for the skyway. She was offered $6,500 for her two-flat. Having refused, her home was condemned by the city. She was living without heat or water and faced eviction.

(Chicago Tribune)

“I think these older people feel they’re being pushed around, that something is being taken from them,” an investigator said when Field refused to leave. “But I wouldn’t want to put her out. Not while she has that shotgun.”

Chicago’s Last Department store sued for $100,000 in damages, alleging the Skyway prevented customers from entering its building at 10520 Indianapolis Blvd. At the other end of the elevated roadway, the Michigan Avenue Church of Christ claimed the Skyway’s entrance ramp made it “dark, close, uncomfortable, unwholesome, and unfit for church purposes.”

But such complaints had little effect. At the 1956 dedication of the Indiana Toll Road, Chicago’s mayor foresaw great tidings for its forthcoming link with what was originally called the Calumet Skyway.

“This improvement is as much an asset to Chicago as it is to Indiana,” Richard J. Daley said.

But when the Skyway opened two years later, call it what you want — a toll bridge or a toll road — it was clearly a white elephant.

Fewer than half the motorists forecast to use it actually did in April of 1958, its first month in operation, and traffic remained well under expectations for years. That tore a big hole in the ledger paper on which the skyway’s financing had been calculated.

Chicago had issued municipal bonds to raise the cash needed to pay the contractors that built it. A bond is a loan; its holder is due the amount of the loan, plus interest. That’s why they bought the bond, to make a profit. Chicago’s bondholders had been assured that enough coins would be dropped in the Skyway’s collection boxes to keep repayment installations coming their way.

But the numbers didn’t add up; Revenue generated by the Skyway was far less than what bondholders were owed.

Some conjectured that it was because the name of the road/bridge was confusing. Locals knew the area as the Calumet Region, so the Calumet Skyway seemed a logical choice. But the name was widely used, including by a Chicago suburb known for its raunchy bars.

“Calumet Skyway in itself is not a good name,” the Tribune editorialized. “To a New Yorker it might connote a route to the Calumet City strip tease joints rather than Chicago’s central business district.” The paper suggested “Skyway Express” as an alternative.

Eventually the name was changed. But the Chicago Skyway didn’t attract significantly more motorists than the Calumet Skyway had.

Pricey engineering firms were hired to find out why. “But a truck driver, taxi cab driver, or police patrolman could furnish free advice,” the Tribune noted.

Indianapolis Boulevard paralleled the Skyway, offering a free route to Indiana. The Skyway was further handicapped in 1964, when US Interstate 94 in Indiana crossed into Illinois and was hooked up to the Tri-State Expressway, giving motorists and truck drivers another way to avoid the Skyway’s toll booths.

By 1963, the Skyway’s bonds were in default.

But as time went on and more motorists opted for convenience over cost, traffic on the Skyway picked up, and in 2004 Mayor Richard M. Daley seemed to have found a way for the city to make some money from the road.

Vintage Chicago Tribune

Vintage Chicago Tribune

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The Vintage Tribune newsletter is a deep dive into the Chicago Tribune’s archives featuring photos and stories about the people, places and events that shape the city’s past, present and future.

Daley leased the Skyway to an Australian private fund that, in partnership with a Spanish construction firm, paid $1.8 billion to operate the toll bridge for 99 years.

Ald. Ed Burke saluted the deal as “the greatest single financial coup in the history of Chicago,” comparing it to the purchase of Manhattan Island from Native Americans for a few strings of beads.

But the Skyway’s problems, made worse by a scandal at the private fund that had bought the lease, continued. In 2011, investment bankers were warning clients that it was worth zero dollars.

The Skyway changed hands a couple of times in the last decade, most recently with the Australian firm’s deal for a majority stake. Tolls have steadily increased under private ownership, and figure to continue to do so.

Nonetheless, Mayor Lori Lightfoot was the latest city leader to tout the Skyway’s blessings, with her office calling the most recent sale a “win for the city, generating a tax payment in the tens of millions of dollars.”

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