The South Loop: Bar Guide

The South Loop has always been an area people go to unwind. It might once have been the home of brothels and burlesque theaters, but these days you are more likely to find a cocktail than a cabaret. There’s no shortage of places to grab a drink within walking (or staggering) distance from the Paragon and whether you’re looking to hide with a beer in a dark corner, or enjoy a cocktail with friends in a well curated venue, there’s something for everyone.

KASEY’S TAVERN
One of the oldest bars in town, this joint exudes old school charm. There’s always a $4 craft and $3 macro beer, making it a great spot for a happy hour meetup or night cap. With 30 beers on tap and twice as many in bottles and cans, there should be something for everyone. You can sample a range of local craft beers guided by the expert bartenders, or simply grab a pint of lager and some pizza while you watch the game on one of their televisions.

ACADIA
If you don’t feel like springing for the incredible full dining experience at Acadia, you can belly up to the bar and enjoy some of the city’s best cocktails. You can enjoy a Hemmingway Daquiri, locally made tonics with a selection of gin. Michael Simon heads up the cocktail program and is constantly innovating new and exciting drinks. Turn up, and put your evening in his hands, and you won’t be disappointed. Their “forager’s and hunter’s tipples” menu includes the Maine Campfire, which blends rye, mezcal, cedar, juniper and honey elixir, tobacco and cocoa nib tincture, while the Local Agent is a mix of vodka, gin, Acadia’s own pale vermouth, preserved lemon, orange peel, and olive ice.

REGGIE’S
This is the place to go if you’re a music lover. If the televised performances, posters, and memorabilia don’t give it away the live performances will do. Reggie’s Music Joint and Reggie’s Rock Club are two distinct spaces, with the latter being a venue for those not old enough to enjoy the bar’s excellent local craft beer selection. Don’t miss the rooftop bar’s basketball hoop and pool table either. The intimate venue with its exposed brick and bulbs has a divey feel, but unlike many concert joints you won’t feel gouged by their reasonable drink prices.

SX SKY BAR AT HOTEL ESSEX
With a standout view of Grant Park and an excellent cocktail menu, this sixth floor spot is quickly becoming a destination for locals as well as hotel dwellers. The bar’s retracting windows allow views of Buckingham Fountain, the Bean, and the Museum Campus. You might have heard about the $669 Dominatrix, a cocktail made of Dom Perignon Brut, Clase Azul Reposado, orange liqueur, candied oranges, lime, and agave, and served in a crystal vase but fear not, there are more affordable options. Highlights include great renditions of classics like to eold fashioned, and signature drinks like the smoke screen, made from Unión Mezcal, Cointreau, hibiscus and fresh lime.

BUDDY GUY’S LEGENDS
If you want to hear the blues played like it should be, you can’t go wrong here. blues sets and jam sessions (be warned: some have $20 covers) most nights of the week, and free, all-ages acoustic shows for lunch and dinner. If you get lucky you may even see legendary blues guitarist and singer George “Buddy” Guy enjoying a show from a seat at the bar. The drinks might seem pricey, but they are pretty stiff, luckily you can grab some delicious soul food and to soak up the booze while you soak up the blues.