The Windy City serves up the wonderfully weird and quirky, especially if you know where to look.
Oregon’s Portland doesn’t have a monopoly on “weird,” as its unofficial slogan might lead you to believe. Find the bizarre, the curious and the wacky alive and well in Chicago.
Belly up to the bar early at Big Joe’s, where turtle racing has been a mainstay on Friday nights. Rooting for the fastest slow-moving animal on the track has never been so thrilling, especially when it involves cheap drinks in one of Chicago’s quintessential watering holes.
To satisfy late-night hunger (perhaps after watching a few turtle races), head to the Weiner’s Circle for a Chicago style char-dog (no ketchup) and a side of verbal harassment from the famously sassy, profanity-loving cashiers who serve the after-hours crowd, many of whom come simply to participate in the fun tit-for-tat spectacle. (The char-dogs are great, by the way, as is the entertainment that typically ensues at this cash-only hot dog stand after midnight.)
Forgo the popular museums for the bizarrely niche ones, such as the Leather Archives & Museum, a surprisingly serious preservation and education of leather, kink, BDSM and fetish lifestyles; the International Museum of Surgical Science
, where macabre exhibits include preserved body parts and a vintage iron lung; or the Busy Beaver Button Museum, a small-but-mighty (and free!) museum boasting more than 9,000 historical pin-back buttons.
As for tours, why not brag to friends about becoming a Chicago murder expert — the historical kind, of course — with Chicago Crime Tours
, a luxury limo bus tour that highlights infamous Chicago crimes and serial killers, or the Untouchable Tours
, a two-hour excursion led by costumed “wise guys” that travels to notorious sites of murder and mayhem from the Prohibition era, when Al Capone was the unofficial mayor of Chicago.
Continuing with that theme, end your night at The Drifter, a 20s-era speakeasy in the basement of the legendary Green Mill Tavern, where drink menus are presented on tarot cards and magicians and burlesque dancers are among the nightly entertainment.