In Chicago you can take the chocolate tour, the gangster tour, the architecture tour…why not the sex tour?

Starting this weekend, Crain’s Chicago Business real estate reporter Dennis Rodkin will lead groups on his fascinating (and not too X-rated) Sexual History of Chicago tour.

Here, some of the raunchiest Chicago facts we bet you never knew:

Sex Tour 1
Rachel Murray/Getty Images

Hoppy To Meet You

Hugh Hefner saw his first naked lady at a figure-drawing class at the Art Institute of Chicago, circa 1946. He was 20 at the time. Unclear if she was in bunny ears or not.

Sex Tour 2.2

Pill Pioneer

Chicago heiress Katharine Dexter McCormick (shown here with husband Stanley) smuggled birth-control pills into America in her luggage in the 1920s.

Sex Tour 5
Evening Standard/Getty Images

He Got Plastered

In 1968, 19-year-old rock groupie and Chicago native Cynthia “Plastercaster” convinced Jimi Hendrix to make a plaster cast of his, um, member in a suite at the Chicago Hilton.

Sex Tour 6

Knowledge is Power

Where the Harold Washington Library now stands was once the site of a beloved brothel. (The farmers who frequented it would have their wallets stolen from their jackets thanks to sliding panels built into the walls.)

Sex Tour 7

Driving Forces

The Dan Ryan Expressway (specifically, the 2700 S. block) was once the site of Tiny & Ruby’s Gay Spot, a hugely popular 1950s lesbian bar. Proprietresses Tiny and Ruby played big-band jazz like nobody’s business.

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