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

Best Bars to Ring in a Special Birthday

… your 30th NEW Tippling Hall You’re old enough to appreciate a good drink but young enough to stay out until the wee hours, and this expansive new spot fits both bills. Open till 5 a.m. on Saturdays, it has a 24-page drink menu with excellent options for all of your party people. River North, … Read more