Best Bars to Do a Craft Shot

Table, Donkey and Stick If you’re game to try the Brooklyn booze trend dubbed the pickleback—a shot of whiskey chased with pickle brine—order one at this Alpine-inspired bar/restaurant with an inviting back patio (enclosed and hearth-heated during winter). Bartenders pair bourbon with rotating brines (cauliflower, onion, leek) for kicky 20-and 30-somethings, whose faces often contort … Read more

Best Bars to Drink Before or After the St. Pat’s Parade

Beverly’s beloved South Side Irish Parade (March 15) runs down Western Avenue, and though the street is lined with Irish pubs, the two best are next-door neighbors. Both pour Guinness, of course. But they’re also the most iconic and most likely to be frequented by in-the-know neighborhood revelers. Keegan’s Pub (10618 S. Western Ave.) is … Read more

Best Bars to Hold a Book Club Meeting

At the Red Lion Pub (Lincoln Park, 2446 N. Lincoln Ave., redlionchicago.com), bookshelves line the walls, and rooms are themed (English history, World War II, African studies). Named for Oscar, the Wilde Bar & Restaurant (Lake View, 3130 N. Broadway, wildechicago.com) has its own “grand library,” complete with fireplace. Both bars have a mature ambiance … Read more

Best Bars to Listen to Live Music

JAZZ Jazz Showcase College kids hang with jazz lifers at this 68-year–old joint, the only spot in town that books an all-star lineup and takes reservations. Cover isn’t cheap—tickets run up to $40 on weekends—but that extra dough gets you access to such vets as Pat Martino (playing a six-show residency this month) sans those … Read more

Best Bars to Get a Drink on the Milwaukee Avenue Bike Lane

The warming housemade cinnamon whiskey at Frontier (West Town, 1072 N. Milwaukee Ave., thefrontierchicago.com) is best enjoyed beside the beer garden’s roaring fireplace: the ideal way to thaw frozen biker fingers. Farther along your commute north lies Revolution Brewing (Logan Square, 2323 N. Milwaukee Ave., revbrew.com), where the bar—and bike racks outside—is always nearly full. … Read more

Best Bars to Take Out-of-Town Guests

The J. Parker The panorama of the park, lake, and skyline delivers the best bang for your buck in terms of city views year-round, thanks to the Hotel Lincoln’s brand-new retractable glass dome. For visitors trying to cram lots of Chicago into a single night, this rooftop spot is a no-brainer. What to order: Midwest … Read more

Best Bars to Get Educated While You Drink

The owner of the Chipp Inn (Noble Square, 832 N. Greenview Ave.) can school you on the city’s beer history post–Great Chicago Fire. Hint: It involves “trainloads of Schlitz.” At Inner Town Pub (Ukrainian Village, 1935 W. Thomas St.), you’ll find patrons of all ages sipping PBR while glued to arthouse films and documentaries.

Best Bars to Drink At from Midnight to Noon

Midnight to 1 a.m. The Logan Theatre Because it screens cult classics at 11 p.m. on weekends. Grab a craft brew on your bathroom break. Logan Square, 2646 N. Milwaukee Ave., thelogantheatre.com 1 to 2 a.m. NEW Celeste Because you’re unlikely to encounter stumbling, party-hearty types. River North, 111 W. Hubbard St., celestechicago.com 2 to … Read more

Best Bars to Go on Your Next Date

Scofflaw This place delivers the perfect ambiance: It’s intimate (but not over the top), quiet (but not pin-drop silent), and equipped with the a­­ll-important fireplace. Arrive before 7 p.m. to nab a spot in the smaller, less bustling back room, where the clustered chairs and couches let you cozy up while you chat. The tunes … Read more