A Chicago Cocktail Crawl

Chicago bars have a way with a resonant cultural reference.

One is named after a late-1800s White Sox outfielder turned temperance evangelist. A cocktail pioneer in another part of the same neighborhood is named after a renowned street photographer. A 10-minute walk away is a gin-centric bar whose name comes from a word coined to describe those who drank illegally during Prohibition. And popping up in unexpected places is the name of Nelson Algren, the author of “The Man With the Golden Arm,” and perhaps most pertinently, “Chicago, City on the Make.”

Cocktail bars across the country are pouring the past (resurrected recipes, speakeasy motifs, barkeeps with Smith Brothers beards) and earnestly so. In Chicago, some of the most engaging bars seem to specialize in what could best be described as studious fun. The history lessons come with a lilt, and the innovation with an intense enthusiasm.

Logan Square, on the northwest side of Chicago, is a locus of interesting, grown-up drinking. An excellent base camp from which to explore the area (and beyond) is Longman & Eagle, a restaurant and bar where travelers can also book a diligently designed room upstairs. (The bar is a fine place to have a Root & Rye cocktail made with root tea, Rittenhouse rye and the mellow, wine-based amaro called Cardamaro.)

Algren never slept here — it opened in 2010, 29 years after his death — but some of his words live on a Longman & Eagle wall, much-quoted lines from the novel “A Walk on the Wild Side”: “Never play cards with a man called Doc. Never eat at a place called Mom’s. Never sleep with a woman whose troubles are worse than your own.”

Billy Sunday

“It certainly was not without a sense of humor, naming a cocktail bar after a gentleman who spent the majority of his life preaching against the evils of alcohol,” said Alex Bachman, the bartender at the animated spot across from the square that gave the neighborhood its name.

But it wasn’t necessarily intended to mock, either: “One thing I definitely admired was, he had a great conviction to what he believed in,” Mr. Bachman said. (Then again, Billy Sunday the outfielder had a lifetime batting average of .248.)