The Dil Pickle: An Inspiration to Expand Nightlife Options Everywhere

5 ideas to get entrepreneurs started and

draw new crowds out of their homes

Growing up in Chicago, there were magical places from the city’s past that no longer existed. Many of us swooned over their memory, mourning the fact that we would never personally know their wonders: Riverview Amusement Park and the White City of the 1893 World’s Columbian Exposition, which left behind the building that is now the Museum of Science and Industry, most stand out.

Lesser known but what captivated me even more was the Dil Pickle Club — a free-wheeling, free-thinking outpost down a narrow alley in what is now the Gold Coast neighborhood. Guests who had to climb a high stoop and duck their heads to pass through the low entryway were greeted by a sign reading: “Elevate Your Mind to a Lower Level of Thinking.”

Open from 1917 to 1935, the Bohemian Dil Pickle flourished in the 1920s, frequented by scientists and social workers, artists and academics, hobos and prostitutes, religious zealots and political radicals, journalists and novelists…luminaries of the day like Carl Sandburg, Clarence Darrow, Lucy Parsons, and Upton Sinclair.


A lover of pub culture but more interested in conversation and oddballs and free speech than in listening to bands, I had a longtime goal of resurrecting the Dil Pickle — as “Conspire.” It was the 90s and 00s, when one-word names for nightspots were starting their own heyday. But now I have a kiddo and go to bed by 9 most nights, so that is on hold. But I have not let go of the idea that the world needs more nightlife options:

  • Fewer things to watch, more ways to participate.

  • Less alcohol, a wider range of fun.

  • Greater options to get introverts out of the house, and additional ways for the social to socialize.

  • Keeping the nightlife vibe and aesthetics of taverns and dance clubs, but having different offerings than ear-shattering, chest-thumping music or pool-darts-jukebox.

Entrepreneurs, there’s room for expansion, creativity, and profit in this space. Especially now as the people of the world have discovered with months of semi-confinement just how and how much they might prefer to be with others out in the world. Give us something new. Feel free to take or riff on these five ideas.


Conversation and Debate Clubs This is what I wanted for my Conspire club. It would be an unabashed nod to the spirit of the Dil Pickle: A rollicking and offbeat nightclub centered around conversation and debate — smart; engaging of ideas low-brow, high-brow, and everything in between; and open to all comers — with a secretive, behind-the-red-velvet curtain ambiance. From the Latin conspirare, “to breathe with,” Conspire’s breathing with would refer to the intense tête-à-têtes its private alcoves would afford as well as the crowdsourced energy generated by its nightly spirited debates.

Learning Societies These I see as more subdued, serious versions of the above, epitomized by my idea of So True, a private club/bookstore devoted to nonfiction books, with nightly book programs by authors or lectures by professors. During the day, members could slip in to escape the hustle and bustle of the big city and enjoy an espresso or a brandy served by a tuxedoed concierge while devouring some cerebral tome from a stuffed armchair. The latest and greatest nonfiction reads as well as the classics of philosophy, science, history, and more would be available for purchase. You could “put them on your tab.”

Non-Alcoholic, Mocktail Bars Mocktails, non-alcoholic cocktails, often with all the ingredient fussiness and presentation fanfare of a craft cocktail, are appearing on more and more bar menus. And trendwatchers do not think it’s going away. The next step is to create more night spots that serve only non-alcoholic beverages — mocktails, juice blends, smoothies, alcohol-free beers and wines, coffee concoctions, specialty loose-leaf teas, powered-up power shots. Keep all the nightlife vibe, just lose the buzz.

Moxie’s is the best name I’ve come up with so far for a mocktail bar. I first thought through this idea when I was recovering from a concussion and couldn’t drink. Then, my best name was the facetious Hard Knocks — you know, for those couldn’t drink due to head injuries, recovery programs, pregnancy. I don’t recommend this name.

One social benefit of a growth in mocktail bars is giving those 16+ or 18+ a cool place to hang out without illicit substances. It might also ease adolescents into an adulthood where adult beverages aren’t a requisite for all socializing.

Board Games Make your public house a Boarding House, a bar devoted to board games. I’ve been to a handful of bars known for their closet full of board games available for patrons, but I envision something a notch up. WWDPD? What would the Dil Pickle do? The Dil Pickle would probably have theme nights, tournaments, all-night marathons. It would actively be involved in encouraging their patrons’ participation and taking things to the next level and not just passively storing some excellent games in a cupboard. You walk through the door, you’re sitting down with friends or strangers to play a game.

Introverts Unite The Silent Book Club is a worldwide network of local silent book clubs — people who get together to each read their own book alongside others who are each reading their own book. Some clubs meet in bars and that’s where we pick up this trend. Why not bars — or private clubs, as long as I’ve opened that door — catering to introverts, especially the pro-social who may like to get out and be around people without necessarily talking to them (much). Quiet, atmospheric, low-light places for thinking, reading, working, listening to one’s headphones. Leave a deposit and the bartender loans you a booklight.

In short, to get more people out more often, expand our nightlife options!

* affiliate link