A barfly's guide to Logan Square, Chicago

From interesting brews to craft cocktails, this northwest neighborhood's libations are sure to please even the most discerning Windy City bargoer.

by Matt Kirouac

Chicago boasts some of the best bars in the country, with drinking establishments of all styles spanning the city’s myriad neighborhoods. From cocktail tasting menus at The Aviary in Fulton Market and $100 daiquiris made with rare spirits at downtown’s Milk Room, to culinary-inspired craft beer at Moody Tongue’s newly opened Pilsen tap room and tiki tipples at River North’s Three Dots and a Dash, it’s easy to drink well in the Midwestern metropolis. Over the past year or so, one neighborhood that’s emerged as a bar Mecca is Logan Square, a northwest side enclave brimming with more booze than people.

Pioneer of the craft cocktail


The Whistler

Logan Square, conveniently situated along the CTA Blue Line between O’Hare International Airport and downtown Chicago, can lay claim to being one of the birthplaces of Chicago’s craft cocktail boom, thanks to groundbreaking spots like The Whistler. The nondescript music venue/cocktail haunt is still packing in the crowds for its ever-changing arsenal of seasonally inspired mixed drinks, like the green-hued Masa Verde made with mezcal, absinthe and verdita, or the cozy Mothership Connection with cold-brew coffee, rum, lemonade and pineapple.

This is also where Paul McGee, one of the most renowned and talented mixologists in the country, made a name for himself before skyrocketing to fame with crowd-pleasing bars like Lost Lake 71. Located just up the street from The Whistler, this tiki wonderland transports guests to a tropical oasis filled with irreverent drinks, quirky glassware, twisty straws aplenty and a general beach party vibe. Drinks change fairly often, but some noteworthy hits include Stranger in Paradise with tequila, Rhum Agricole blanc, pineapple, Falernum, cinnamon, allspice, angostura bitters and absinthe; and A Lonely Island Lost in the Middle of a Foggy Sea, which contains two kinds of rum plus Rhum Agricole blanc, coffee, pineapple, lime and Demerara.

Elsewhere in the ‘hood, drinkers can sip habit-forming Negroni slushies at Parson's Chicken & Fish 78, a sprawling watering hole with quenching slushy concoctions and other mixed drinks like Oaxacan On Sunshine (El Buho mezcal, Cocchi Americano, grapefruit, habanero, soda, red wine) and Pineapple Punch (Plantation Pineapple Rum, Aperol, pineapple juice, lime, tea, Angostura Bitters).

Photo by Clayton Hauck for Parson's Chicken & Fish

Parson’s signature Negroni slushy

A couple blocks west of Parson’s is Scofflaw 72, an ode to gin with lip-smacking combos like aperol, cantaloupe, fresno chile and gin. Come on a brisk winter night and perch by the fireplace for a truly memorable evening. Continue your cocktail crawl even further west along Armitage Avenue with a stop at Best Intentions for boozy horchata and herbal milkshake-like drinks that taste like mint chocolate chip ice cream.

The best of the breweries


Revolution Brewing

While cocktail bars continue to establish themselves all over the neighborhood, Logan Square is also home to some exemplary breweries and taprooms. Revolution Brewing 75 popped up on Milwaukee Avenue well before the neighborhood was the hot spot it is today, churning out a lineup of brews like its famed Bottom Up Wit, Eugene Porter and Anti-Hero IPA. Shortly after the brewpub began packing in the crowds, Revolution doubled down with another facility a bit north on Kedzie Avenue. The industrial space is where Revolution does most of their brewing, and patrons at the bar can get an up close and personal peek at the process while they sip their ale.

One promising newcomer is Hopewell Brewing Company, a slick and inviting taproom with a modular interior reminiscent of something out of an IKEA catalogue. And that’s meant in the most complimentary way possible. The sunny space sports highly drinkable brews like its mouthwatering First Lager, its 24:37 Red IPA and the tangy All Hope Kettle Sour. Hopewell stocks a handful of nostalgic board games as well, in case you’re in the mood for Connect Four with your beer.

Don’t forget about wine


Webster’s Wine Bar

Proof that no potable goes underserved, one of the best wine bars in Chicago boasts a prominent locale right at the nexus of the neighborhood square itself. At Webster's Wine Bar 74, a dimly lit nook that feels like a drinking parlor J.K. Rowling would imagine, the bar stocks upwards of 500 bottles, with several dozen available by the glass. Varietals span the globe, with both old-world and new-world wines getting due diligence, and sommeliers are well-equipped to guide you towards something you’ll love. Match your vino with any of Webster’s fantastic plates, designed for sharing and pairing. Items include bacon-wrapped dates, venison tartare and bistro hanger steak.

One new wine bar entry, located a bit further west of the square, adopts a Latin accent for its wine and food. Penumbra Wine Bar features a menu of ceviche and bocaditos, attuned to a miscellany of South American, Spanish and Californian wines.

What’s new?

Fresh bars seem to take shape every day in Logan Square, and there’s an exciting crop of newcomers that have recently opened their doors. This includes Estereo, a Latin-accented nook from established bar group Heisler Hospitality; The Ladies’ Room, a clandestine Chinese drinking den from the hitmakers behind Fat Rice 85; Spilt Milk Tavern, an ode to corner bars of yore with Concord Grape Juleps and boozy soft-serve ice cream; and Mezcaleria Las Flores, Chicago’s first mezcal-devoted bar chock full of offbeat agave spirits and cocktails served in unique “glassware” like gourd husks.

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