The 22 best Chicago Loop bars

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.

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 charitable, order the "cocktail for a cause" to have a portion of your tab go toward a non-profit organization.

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 Trouble Will Find Me, with Cimarrón tequila, mezcal, yuzu soda and watermelon. Just make sure you have a reservation—the wait to get on top of this hotel can drag on for hours.

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 Hospitality, the group behind popular concepts such as Beatnik and Mama Delia, GoodFunk highlights natural wines from eclectic producers around the world. You’ll want to pair your bottles with interesting bites like an anchovy and butter toast or jamón ibérico flatbread, and you should plan to arrive early because the small space fills up fast.

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 longtime 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.

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.

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 CBD-infused pineapple express cocktail. The decor and vintage posters throw it back to yesteryear, but the karaoke and late-night dance music add modern flair.

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.

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 salmon rillette topped with caviar. On Sundays, Bar Pendry also offers boozy afternoon tea service.

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 Capybara, an tasty blend of Brazilian cachaça, starfruit and mango juice. Pair it with an order of the fan-favorite empanadas, which are stuffed with chicken and served with aji amarillo salsa.

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.

There’s nothing out of the ordinary at this Loop bar and grill, and that suits the famished financial district clientele just fine. They’re just happy to have a decent option for an off-the-clock cocktail or a quick lunch that’s above bottom-feeder pub grub. The menu offers coconut shrimp, several salads, sweet potato fries and a meatloaf sandwich, which can be washed down with one of 12 beers on draft.

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 live blues music with a menu of classic Cajun fare. There are performances most nights, spanning a variety of genres, so there's always a new act to discover.

Mosey through door at classic Chicago dive bar Sky-Ride Tap during lunchtime and you’ll find mustachioed laborers and Board of Trade employees alike hanging out. After work, it's an easy spot to grab a cheap beer before heading home.

Located in the Chicago Athletic Association, the second floor Game Room bar boasts pool tables, a poker table, chess boards and a full bocce court. You can soak up the booze with warm pretzels, fried chicken sandwiches, chicken wings—just wash your hands before you get back to the shuffleboard.

Weather permitting, this live-fire cooking concept inside the Willis (Sears) Tower has one of the best rooftops for post-work happy hour. Any other time of year, you can hang out in the giant, multi-floor indoor space and enjoy decadent Italian beefs, oysters, wood-fire meats and an array of classic cocktails.

For the more active partiers, AceBounce has everything one could need. This entertainment venue/restaurant in the Loop brings out the competitive spirit with ping pong matches for just $10 per person (for 55 mins). Dive into the additional gaming options like Ping Pong X, which features AI tracking technology, or beer pong to relive the old glory days. On Thursdays, guests can enjoy unbeatable $5 play and pour deals.

Originally Revival Food Hall, the name's the only thing different about this beloved collection of good eats. You love Sterling's lunch offerings, but did you know that the bar stays open till 8pm Monday through Friday? Saddle up for a classic cocktail, wines by the glass or beer—all of which are relatively affordable for the area.

The original North Center outpost of pioneering Chicago cider bar the Northman closed in early 2020, but the business's Riverwalk beer and cider garden is still pouring drinks. Sit down and enjoy an extensive selection of ciders and local craft beers, accompanied by a menu of sausages, salads, pretzels and bar snacks. Located on the shaded eastern portion of the Riverwalk, the Northman is also dog- and kid-friendly—we'll raise our glasses to that!

Come summertime, Chicago winos slip down to the Riverwalk for people-watching and a bottle of vino. The sprawling outdoor patio rides the Chicago River, making it an ideal place to lounge around after work or on the weekend. Choose from glasses of pinot gris, rosé, riesling, cava or syrah to enjoy while you gaze at the boat tours floating by.

If sipping a Mai Tai next to a body of water is what your heart desires, head to Island Party Hut on the Riverwalk. You'll feel the tropical vibes once you see the fake bamboo trim and thatched roof of the bar, where you can order a tiki drink served in a plastic cup.