The best South Loop bars and nightlife

Acadia has a lock on the best cocktails in the South Loop, and you don't have to shell out for a spot in the dining room to drink them. Head to the casual bar area, order a lobster roll or burger, then work through the thoughtful cocktail list with drinks like the Hemingway daiquiri, plus drinks like Gins/Tonics/Limes, a spritely take on a gin and tonic with housemade lemongrass tonic and kaffir lime and cucumber ice cubes.

If you show up at the club, you may just see Buddy Guy sitting at the bar, overseeing the whole operation: He’s more than just a name on the sign outside. There are also free acoustic sets during lunch and dinner most days of the week. And if you like Louisiana cuisine, the kitchen has what you need.

Long heralded as Chicago’s leading jazz venue, the venerable club has been forced to relocate more than once since its inception in 1947. However, since moving to swank new digs in 2008, the Showcase has easily reestablished its reputation for bringing in top-shelf talent like the Bad Plus and Miguel Zenón.

The people-watching at Kasey’s is almost as good as it is from the benches around the Printers Row fountain, but this popular watering hole’s got beer. And pizza. Advantage: Kasey’s. You’ll recognize the same Irish-English-pub vibe from up north, and you may spy a frat rat, but generally the crowd–like the bookish, lofty-artsy neighborhood–is mixed, especially when it comes to baseball loyalties.

In case you missed all the concert posters, the flat–screens showing performance footage or the corner stage (which, more often than not, has a band on it), live music is the theme of this South Loop pub. But with such a good beer selection and a friendly staff, you don’t need to be into the music to want to spend your night here. The punk sanctuary draws the youngest crowds into its two distinct rooms—Reggie’s Music Joint and Reggie’s Rock Club. The latter is the rare strictly underage club in the city, and heir to the deceased and beloved Fireside Bowl.

The address is different (the original location was a few blocks east), but the booking policy remains the same at this pioneering venue and informal showcase for members of Chicago’s trailblazing Association for the Advancement of Creative Musicians. The club, which was run by veteran saxophonist Fred Anderson before his death, concentrates on improvisational jazz.

If Chicago is a city of neighborhoods, every neighborhood could benefit from a place like Vice District. It’s not the biggest brewery, it’s not the craziest, and it’s not lager-dedicated or hop-crazy or Belgian-inspired. It’s just a good local place that makes small-batch beer. Vice District has a couple of core beers you should try, along with a rotating selection of others that will bring you new reasons to make it to South Michigan Avenue.