The 17 best Chicago Loop bars

You'll feel like a million bucks when you walk into the Kimpton Gray's loungy library bar, Vol. 39. The space—which is dotted with leather couches and lined with books—exudes elegance. The beverage program matches the tone with a variety of cocktails inspired by nostalgic flavors and experiences. If you're feeling splurgy, order the Vol. 39 Vintage Old Fashioned with a house blend of cognac, armagnac and calvados. At $35, it's an investment, but it's totally worth it.

An enduring watering hole from a bygone era, Miller’s Pub has been pouring cold pints for local workers since 1935. In its heyday, the bar was frequented by celebrities and notable sports figures like Harry Caray. Today, you can expect to see longtine regulars as well as tourists gathering for stiff martinis and tasty slabs of baby back ribs. And in stark contrast to the rest of the neighborhood, the doors stay open until 2am every night.

Hidden away inside the Chicago Athletic Association is one of the city’s best craft cocktail bars. Milk Room, an intimate eight-seater by Land and Sea Dept., specializes in classic drinks featuring rare spirits. You can browse through a selection of vintage whiskeys or options like 1970s Fernet Branca and 1940s Cointreau. But if you desire a specific concoction, the talented mixologists can also make it happen. It won’t come cheap, yet there’s no other experience that compares. Reservations are required and available here.

Oenophiles and those in search of a post-work drink would do well to head to this lively European wine bar overlooking the Chicago River. Run by Bonhomme Group, the team behind popular concepts such as Beatnik and Porto, GoodFunk highlights natural wines from eclectic producers around the world. You’ll want to pair your bottles with interesting bites like a foie gras shooter and jamón ibérico flatbread, and you should plan to arrive early because the small space fills up fast.

For decades this cavernous Loop tavern has cornered the market on medieval Chicago dives. Beyond the heavy doors that seem to hide a monastery, you’ll find an after-work crowd downing beers. The beer list is formidable and usually includes some rare offerings from local craft breweries as well as imports from Belgium and Germany.

You've likely seen an Instagram post (or four) taken from the Chicago Athletic Association Hotel's rooftop bar, which offers some of the finest, unobstructed views of Millennium Park and Lake Michigan that you'll find in the Loop. Once you're done snapping an obligatory picture, sit down at Cindy's and enjoy well-crafted drinks like the Figgy Stardust, with mezcal, fig liqueuer, lemon and orgeat. Just make sure you have a reservation—the wait to get on top of this hotel can drag on for hours.

Even in the dead of winter, this beautiful rooftop bar at the Kimpton Gray Hotel feels like a tropical paradise. The menu here highlights South American flavors in drinks like I'll Be Better in the Morning, an addictive blend of plantain-infused Scotch, black walnut tiki bitters and Drambuie. Pair it with an order of the fan-favorite empanadas, which are stuffed with chicken and served with aji amarillo salsa.

A rooftop bar situated in a prime location, Raised draws crowds when the temps rise. On the third floor of the Renaissance Chicago Downtown Hotel, guests get unobstructed river and skyline views that rival highrise rooftops. Toss in botanically inclined cocktails and a menu of inventive small plates, and you've got the perfect place to perch on a sweltering summer evening.

True to form, Brando’s Speakeasy is not what it seems. It’s a lounge, yet conversation flows more like a neighborhood haunt. The cocktail menus features interesting drinks, like the root beer old fashioned. The decor and vintage posters throw it back to yesteryear, but the karaoke and late-night dance music add modern flair.

Cozy up next to the fireplace at this classy bar inside the Pendry Chicago hotel. You’ll feel like old money as the space drips sophistication with features like floor-to-ceiling curtains, leather sofas, vintage rugs and a curated art collection. The menu focuses on classic libations alongside contemporary creations so do your best impression of Don Draper by sipping on an old fashioned, and perhaps complementing it with a decadent bite of fried chicken topped with caviar. On Sundays, Bar Pendry also offers boozy afternoon tea service.

The legendary, century-old German haunt has added a few modern dishes to the menu over recent years (bacon-wrapped shrimp, cedar plank salmon), but we stick with the way things were. The bar still pours Berghoff beer and root beer, the kitchen still slings Wiener schnitzel, sauerbraten and the like, and the crowds still pack ’em in.

The expansive bourbon-based menu at 2Twenty2 Tavern is crafted weekly by cousins Chris and Jake Mannos, heirs to the Exchequer Restaurant & Pub. The spot offers the usual accouterments—live music, sporting events and bar games—but in a dimly-lit, rustic pub environment accented by fireplaces and whiskey barrels. The cocktail concoctions encompass spins on classics like margaritas, mules and Manhattans, while the bar bites include buffalo cheese curds, fried pickles, tavern-style pizzas and burgers. Come for the giant Jenga and shuffleboard, stay for another drink.

Owned by one of the city's few remaining musical legends, this club mixes up nightly live blues music with a menu of classic Cajun fare. If you want to see Buddy playing in the club that bears his name, mark your calendar for January, when he usually holds down a month-long residency.