WBEZ's Curious City audio blog explains that Chicago hoped to be America's aviation hub all the way back in the 1920s—for airships. But it's not the ideal environment in which to dock them:
When it comes to Chicago buildings that may or may not have had airship docking infrastructure, we encounter only a few leads. One involves the Blackstone Hotel. In a 1910 article from Chicago’s Inter-Ocean newspaper, the Blackstone’s manager confirms plans to build “Drome Station No. 1” on the rooftop — big enough for four airships, housing stalls and a repair shop. The manager said it’s “not a whim nor advertisement” for the newly-opened hotel. Today, though, there’s no evidence the Blackstone’s rooftop landing dock ever existed.
“Docking a large rigid airship to the top of a building is one of the worst ideas anyone could ever come up with, which is why it was never done,” he says.
Airships could be 800 feet long, and a single mast atop a building could provide just one point of contact for tying off. If an airship were moored only at its front, changing winds could spin the ship in circles. In the case of the Club, that would have meant a docked airship could swing into nearby skyscrapers, like the Tribune Tower. It would have been a disaster waiting to happen.
Of course, Chicago eventually became one of the world's principal aviation hubs, but not with lighter-than-air craft.