Unlike the city’s rock venues, most of the shows for downtown dance and theater establishments let out early enough to leave you jonesing for a cocktail before moving on with the evening. And while plenty of Chicago’s top entertainment spots are centrally located in the Loop, many of the bars there cater so shamelessly to tourists you couldn’t pay a real Chicagoan to drink there. We’ve singled out a few of our best choices for post-show drinks and ironically, many are tied in with hotels (which by nature cater to out-of-towners). Still, we won’t let that stand between us and a good cocktail.
Slightly hidden on the corner of Lake and Wells underneath the El tracks, Monk’s is cozy, unpretentious and fully stocked with the brew, wine or spirit of your choice. In addition to the well-rounded drink menu, Monk’s also has one of the tastiest burgers in the Loop. The pub’s patrons and servers are the friendliest you’ll find, and the mix of easygoing chatter and fairly priced drinks make the downtown bar feel more like your neighborhood joint. Just be sure you stop by during the week; Monk’s shuts down on weekends.
Hidden next to the grand lobby inside The Palmer House, Potter’s style is pure Chicago class. The upscale lounge is tastefully luxe and intimate, with plenty of tucked-away tables and private booths that are perfect for a quiet conversation over a pair of small plates and artisan cocktails. Pick this bar in particular if your post-theater cocktail crew knows their booze: the service and bar knowledge is first rate, making it a perfect place to order a high quality (and slightly obscure) drink that you can’t always find elsewhere.
Formerly a basement bar underneath Pops for Champagne, The Watershed received a makeover that rubbed out all traces of its clubby, so-last-decade past. The joint was transformed into a super-cool speakeasy-style hangout filled with high-back Pullman booths (a nod to Chicago’s Pullman car-producing past), mismatched vintage table ware, local spirits, regional beers and cleverly named, old timey cocktails. If you get hungry, the bar shares a kitchen with Pops, which has a knack for producing hearty, surprisingly unfussy eats.
ROOF on theWit
Easily one of the hottest nightlife spots in the city, ROOF sits atop theWit hotel offering one of the best 360 views of downtown. To match the dramatic setting, the food and drinks are equally impressive, with edgy cocktails and creative menu bites that change by the season. The downside of having food and drinks served to you 27 stories high with a killer view of the Loop and the lake shore as your background: the wait can become insanely long, and reservations are only accepted with a food and drink minimums starting at a thousand bucks.
BIG Bar & Brasserie
151 E, Wacker Drive
Near The Harris Theater
Nestled inside the Hyatt Regency, BIG Bar owes its name to its sprawling bar top that partially stretches around the perimeter of the lounge and to the fishbowl-sized cocktails that leave your head swimming. The decor may be a little Vegas-style cheesy for a downtown bar in an otherwise classy hotel, but if you can get past that, the views overlooking the river are worth enduring the day-glo color scheme. Plus, appetizers like short ribs and brioche bun sliders are extra tasty – and make you look just the slightest bit more sensible when you pose next to your 48 oz martini for the inevitable camera phone snapshot.