Want to take a historical tour of Chicago, IL’s most storied pop culture spots? You won’t have to look far to get the deed done. Think about this city’s history: Route 66 starts in Chicago. Soap opera was (supposedly) born here. The Chicago River runs in reserve; it’s the only river in the world that flows backward. PBR? Yup, that brew was first poured in Chicago. Rotary International HQ is in Chitown, too (OK, Evanston, technically). Twinkies, brownies, zippers, skyscrapers, deep-dish pizza … yep, all trace their origins back to the Windy City. And don’t forget about Barack Obama. It’s a city of first, not seconds. So if you’re in town, and really want to take a tour that can help you experience the best the city has to offer? Here’s a list of ten great ideas – and many more spots to hit – that can help you get a sense of the city’s long and influential pop culture history.
Images of Hugh Hefner’s blond cohort of hyperhealthy ladies sprawling in the grotto may be geographically synonymous with California sun and fun. But before he moved west, Hef held court in the (basement) grotto at 1340 North State Street, a pretty cool building, where the first Playboy Mansion stood. Here he ran his empire for many years. The mag itself began from Chicago in 1953, and in fact, the first bunny-staffed Playboy Club opened in 1960 at 116 East Walton Street. It was basically an adult version of a multifloored amusement park stacked, layer upon layer, floor upon floor, with orange as the crucial accent color (Hef was a big fan of orange). During the early 1960s, shortly after opening, more than 130,000 people visited that Chicago space, which basically made it the most popular club in the world. Pretty amazing stuff.
“Public Enemy No. 1” did his time in Chitown, mostly in East Lakeview (now Boystown, the Windy City’s gay hub). He stayed with his sister while on the lam at 3512 North Halsted, down the road from a convenient Circle K (at one point, he’d go to a few Cubs games in Wrigleyville). He was taken out in the now refurbished Biograph Theater, after sitting in the exit-friendly 12th row, eventually expiring in an alleyway. His corpse was placed in the Cook County morgue and while on public display, was (reportedly) viewed by more than 15,000 visitors. The last film shown at the pre-renovated Biograph was Woody Allen’s “Sleeper” in 1974, on the original projector from the gangster era, which furnishes an interesting link to Max, Allen’s character’s son in 1995’s “Mighty Aphrodite,” who nicknames a particular appendage his own “Dillinger.”
Yes, there is a tunnel underground (the owner confirms this). And yes, Al Capone memorabilia does adorn the walls, and yes, there is an interesting alabaster statue of the Greek fertility goddess, Ceres (reputedly named “Stella by Starlight” originally) on-site. Nightly acts play jazz, bebop and improv alternately with another staple at the Green Mill — poetry slams. These maintain the greatness of owner Dave Jemilo’s temple to entertainment, keeping it a must-visit for new and old acts. This place pops up in poignant personal stories to this day, though its longest reach in American history is as a crucial hub during the Prohibition Era, perhaps its most enduring early legacy.
The “El” (short for “Elevated”) is synonymous with the CTA, which is different from the Metra (the rail lines for the suburbs). All CTA lines circle the business district of Chicago, the Loop, in a “loop” (nifty, eh?), and while it often breaks down, inevitably, in winter, it is beautiful and storied — remember Tom Cruise brought Rebecca de Mornay in “Risky Business” on the CTA to make love on “a real train.” While New York’s subway lines during 2017 endured the “Summer of Hell,” Chicago Mayor (pronounced “mare,” rhyming with “bear” as in “da bears”) Rahm Emanuel said New Yorkers should move to Chitown because the CTA doesn’t face nearly as many issues as the MTA. But really, all you need to do is walk through the Loop at night and see flights of stairs listing lines and stops in a line upward to get a sense of atmosphere: Kimball, 54th/Cermak, Linden, Ashland/63rd | Cottage Grove, Harlem, Midway, etc. Pretty cool stuff.
Sure, Tony Bourdain and President Obama can jump to the front of the line to get their trays filled at this Hyde Park landmark, but that’s all the favoritism you will ever see. Comfort food in a diner with lively atmosphere makes this a must-stop place for local lore (and lunch) — the genuine caff-style counter will take likely you back to your own cafeteria days. Luckily there is an ATM too (they take only cash at this august establishment). Kinda fitting, eh? You’ll have money left over from your Jackson, though, and will still be stuffed, as you can eat a hamburger steak, biscuit and mashed potatoes, feel pleasantly food drunk, and walk out with some scrilla in hand. It often seems like everyone, including local politicians, average Joe’s and Jane’s, U of Chicago students, and those looking for bargain bites at a greasy spoon chow down here.
You’ve probably seen the interior in “The Untouchables,” but nothing compares to visiting this incredible early skyscraper, and Chicago’s oldest high-rise building, notable for its exposed exterior steel construction. Most notable, however, and what makes it loom largest perhaps in visitors’ minds, is the luminous Frank Lloyd Wright lobby interiors, spanned by stretches of steel walkways and transport staircases that will make you fall to your knees in awe of the beauty on display here.
You can’t spend time in Chitown without considering the infamous fire in October 1871, which destroyed about 2,000 urban acres. Only a half dozen or so major original structures from the pre-fire period still stand in the city. Then again, the stockyards remained after (but there isn’t much left there now), along with whole other areas of the city, even if most of downtown was incinerated. In certain ways, the fire is responsible for much of Chicago’s stunning modernity, particularly in forward-thinking city planning and architecture: Building codes required that post-fire buildings avoid the use of wood in construction, giving rise to steel and concrete construction. This accounts also for much of downtown Chicago’s logical layout: The city planners, unlike the urban zones and chaotic growth of Eastern cities, had a plan and stuck to it.
Ever wonder why there doesn’t seem to be too much trash on the streets in the city? (Well, Wicker Park is a mess, OK, OK.) Garbage doesn’t collect on street level as it does in Manhattan and get ripe in the heat because Chicago has a network of alleyways where a healthy amount of dumpsters and garbage can be sited (important for escaping gangsters, too, even if Dillinger didn’t quite make it out of the Biograph’s). There are nearly 2,000 miles of alleys in the city; some are even made of wood. Most public transport lines run along alley corridors and routes, which makes for much less congestion when it comes to transit. It might take a little while for you to notice it, but once you do, you’ll realize why the city, while not always as fresh as a summer breeze, doesn’t have breezes carrying the smell of melting trash.
Jazz, the blues, gospel: All of these musical art forms are unthinkable without Chicago. Then there is rock music: Steve Albini. Smashing Pumpkins. Liz Phair. Veruca Salt. And hip-hop: How about Kanye? Or Common. Funk: Curtis Mayfield, Chaka Khan. Soul: R. Kelly. And it’s not a secret that house started here, too, perhaps thanks to the Midwest’s great depth in thrift and secondhand shops, and all those castaway electronics and records. It’s nearly impossible to think of the American music scene without the Windy City. It’s the stuff of legend – be sure to take in a show or ten at several of the city’s more popular hangouts.
Well, we might as well subhead this “John Cusack,” as Cusack’s past is bound up with his home city in his oeuvre and life. But one of the best Chicago movies revolves around Nick Hornsby’s classic 1990s novel, “High Fidelity.” Now, in the book, Rob Fleming moves through London, but in the film, John Cusack’s Rob Gordon circulates through a gritty calque of the novel’s locales. And yes, the 2000 film does an incredible job of reimagining North London as Chicago, which is what the producers, and Cusack, really wanted. Wicker Park, where Championship Vinyl was set in the film (at 1500 North Milwaukee Avenue), was not yet gentrified during film, so the area looks and feels much scruffier than it is now. And, if you take a tour of the locations in the film, you’ll see many still exist, and find that most of them play a part in our list of local lore as well.
David Podgurski has written about travel, books, fashion + entertainment for digital and print media. He’s hunted down vintage finds in crumbling attics, published poetry, worked for the New York MTA, and likes to haunt museums, cafés and shops. When he isn’t traveling or writing, he’s thinking about his next trip — and what to enjoy when he gets there.
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