Chicago is a city with a rich bar history alongside its generous and diverse food culture. With over 2.5 million residents of Chicago proper, and nearly 10 million in the broader Chicagoland area, the city is home to a vast range of bars, from high-end cocktail havens to the epitome of welcoming Midwest dive bars.

Best Intentions
Chicago is a city rife with excellent bars, but none tops Best Intentions since it opened in 2015. Brothers Calvin and Christopher Marty impart their eclectic 1970s dive bar ethos, sense of humor, and warm Midwest welcome to quality cocktails, Angostura bitters on draft, cheap beers, and a wide range of spirits from amari to schnapps.
Drink This: Marty and crew show off less-heralded spirits like apple brandy in unexpectedly nuanced drinks like the Statler (apple brandy, white vermouth, Nux Alpina, lemon, pickled cranberry syrup, Angostura bitters). Their killer burgers or Reuben sandwich pair beautifully with the Jakuzzi, a Martini variation of vodka, Apologue Celery Root liqueur, dry curacao, fino sherry, and Bittercube Bolivar bitters.

Truce
Just opened in June 2024, Truce is a brick- and wood-lined coffee shop with 1970s Kyoto vibes serving coffee, bites, espresso drinks, coffee cocktails, and NA cocktails by day, with more NA and regular cocktails by night. Partners David Mor (of Lilac Tiger, also in this list), Matthew Hunnel, Rami Ezzat, and Sarah Kmiec bring a wealth of experience and seasoned hospitality to this friendly space with their tight team.
Drink This: Coffee from Indiana-based Yaggy Road Roasting Company in delightful espresso drinks like the Black+Gold (espresso, turmeric, ginger, pineapple gum syrup, cayenne, black lime, oat milk). Mor’s cocktails are the star of the show, whether an Absinthe Frappé variation, tall with acid-red absinthe, strawberry, strawberry blanc vermouth, kiwi, and pandan whip; or a Triple Chai Daiquiri with Cynar and amontillado sherry.

Photograph by Virginia Miller
Lemon
Lemon (our featured bar managers interview this issue) is that all-too-rare bar that deftly manages to be laid-back and unpretentious but never boring or safe. It delivers robust hospitality, neighborhood ease, and live performances on a stage at the end of a long bar serving quality house and classic cocktails, shots and a beer, and thoughtful NA options. There’s a vibrant small-batch spirits collection and intentional choices about the best brands to showcase in each individual cocktail.
Drink This: Don’t miss superb versions of rare classic cocktails like the Absinthe Suissesse, a nuanced blend of Tempus Fugit crème de menthe, Meletti anisette, Pernod, Massaya Arak, orgeat, orange flower water, and a whole egg. House drinks also wow, like the Cloud City, a frothy white port, Aperitivo and genepy concoction bright with grapefruit and a whole egg.

Photograph by Virginia Miller
Bisous
Peter Vestinos and the Footman Hospitality team opened Bisous in January 2024 as the sister to their enchanting bar Sparrow. Like Sparrow, Bisous is a romantic, soothing escape from the busy city streets. Different from Sparrow’s 1930s–40s vibe, Bisous takes inspiration from 1960s Paris, with a heavy focus on martinis, highballs, and fortified wine cocktails alongside French and sparkling wines.
Drink This: Classic Gibsons, Pink Squirrels, Freezer Martinis, and Agricole Daiquiris coexist next to delights like the Aristocrat, which combines aged aquavit, apple brandy, oloroso sherry, and blanc vermouth. Everything is done with retro elegance and best enjoyed cozied up in one of their half-circle booths.

Gaijin
Debuting at the tail end of 2019, chef Paul Virant’s quirky-cool Gaijin thankfully survived the pandemic to shine as an okonomiyaki-centered restaurant, showcasing both Hiroshima and Osaka styles of the savory Japanese pancake, alongside kakigori (a shaved ice dessert) and mochi donuts in a skylit, casual space.
Drink This: Bar manager Stella Miller perfects an approachable-yet-thoughtful drink menu ranging from sake to tea. Highballs and kakigori shaved ice cocktails shine, as do cocktails like the irresistible Shiso Delicious: Kiyomi Okinawan rum, tomato honey, fresh shiso,and citrus.

Meadowlark
Debuting in Logan Square late 2022 in a roughly 100-year-old brick-walled building, Meadowlark is an intimate bar, lined with vintage books, leather couches, and lamps under wooden rafters. It has garnered a number of accolades, including being one of North America’s 50 Best Bars.
Drink This: Beverage director Abe Vucekovich crafts creative cocktail menus on inspired themes like birds of the Midwest and the Chicago World’s Fair. Their third summer 2024 menu is “Composition Book Vol. 1,” a whimsical, 16-cocktail tribute to childhood memories, from summer camp to Saturday morning cartoons. One of the best-tasting is the Sleepover, lush and bubbly with umeshu plum liqueur, fernet, BrancaMenta, cinnamon, amontillado sherry, sparkling water, and root beer bitters.

Lilac Tiger
Opened in fall 2023 in West Town by chef Zubair Mohajir, Ty Fujimura, and Won Kim, Lilac Tiger is a tiny, hip South Asian spot fronted by speakers, neon signage, and a 1980s boombox look leading to a tiny interior from an inviting patio. The dishes are lively, like chili crisp Sichuan calamari or vada pav, Indian croquette sliders touched with sesame tomatillo.
Drink This: Beverage director David Mor keeps drinks breezy and leans toward featuringIndian, Korean, and Japanese spirits. Think a chai-laced rum and Indian whiskey Daiquiri or a milk punch of Empirical Soka (a sorghum, melon, cucumber, green apple spirit from Copenhagen), papaya, carrot, saffron, cardamom, and Bruichladdich Scotch whisky.

Asador Bastian
On the dim, inviting second floor of an 1833 townhouse, Asador Bastian hit River North in spring 2023 with a unique steak-meets-seafood theme of Basque proportions. Serving Galician beef with San Sebastián inspirations, chef/co-owner Doug Psaltis’ Spain focus veers from tortilla española to caviar churros and seafood delights like anchovy “mastrimonio,” an anchovy toast.
Drink This: Hidden downstairs is an intimate bar focused around classic cocktails, including a martini and gin and tonic menu section, plus bar bites like foie gras carne crudo. A vintage cocktail section intrigues with spirituous, elegant cocktails featuring vintage spirits from the 1960s and 1970s.

The Bamboo Room
Hidden inside Three Dots & A Dash, The Bamboo Room is the more pleasing, snug side of the larger tiki haven helmed by beverage director Kevin Beary. The spirits selection is an homage to rum and rhum agricole, with an impressive selection of major to obscure sugarcane spirits.
Drink This: The artful, illustrated menu hints at elaborate glassware to come, whether striking parrot tiki mug, glass sea urchin, or fish bowl. Balanced drinks go beyond rum to highlight tequila, cachaça, Japanese whiskey, and the like — as with Money Melon, a parrot tiki mug filled with tequila, rum, shochu, lime, tangerine, pineapple, honeydew melon, and orgeat.
Bar Tre Dita interior, Photograph by Virginia Miller
Bar Tre Dita
With a pasta lab, 44-foot ceilings, and 40-foot windows gazing out onto Lake Michigan, chef Evan Funke’s Tre Dita restaurant opened in spring 2024 as a dramatic second floor newcomer to the towering, 101-story St. Regis Chicago. Bar Tre Dita has a separate entrance, a dramatic bar with black-and-white marble-tiled floors, padded tan bar stools, velvet blue and rust chairs, and loveseats. It evokes Art Deco with a modern touch.
Drink This: Italian-centric amari, grappa, and vermouth star in the dense, 400+ bottle spirit library. Cocktails Tre (Piucinque italian gin, white vermouth, grappa, lemon) and Dita (rye whiskey, Sfumato Rabarbaro amaro, red vermouth, Cynar 70, Luxardo Antica, house bitters) best showcase their elegant Italian ethos.