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Vol. 39
Vol. 39

The 13 best Chicago Loop bars

Drinking downtown doesn't have to be boring—check out the best dives, rooftops and lounges in the Loop

By Zach Long and Morgan Olsen

On weekdays, the Loop is all business, but as soon as the clock strikes 5pm, downtown workers flock to the area's top watering holes for post-work tipples. The best bars in the Loop run the gamut, from swanky cocktail lounges and ritzy rooftop bars to the funkiest, oldest dives in town. And since most of these downtown bars cater to early-evening revelers, you can expect happy hour deals galore. Don't settle for a boring night of drinking downtown—dig into our guide to the best bars in the Chicago Loop.

RECOMMENDED: More things to do in the Loop

Best bars and nightlife in the Loop

Photograph: Jaclyn Rivas

1. Boleo

Restaurants Argentinian Loop

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 the In the Morning, I'll Be Better, an addictive blend of plantain-infused Scotch, black walnut bitters, tiki bitters and smoke. Pair it with an order of the fan-favorite empanadas, which are stuffed with flank steak, red pepper and olives and served with chimichurri sauce.

2. Monk’s Pub

Bars Pubs Loop

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 beer and adding to the piles of peanut shells littering the floor. The beer list is formidable and usually includes some rare offerings from local craft breweries as well as imports from Belgium and Germany.

Photograph: AJ Trela

3. Cindy's

Restaurants Contemporary American Loop

You've likely seen an Instagram (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 Getaway, with gin, Thai banana, pineapple, lemon and sparkling water. Just make sure you have a reservation—the wait to get on top of this hotel can drag on for hours.

Berghoff Restaurant
Photograph: Jonathan Samples

4. The Berghoff

Restaurants Contemporary European Loop

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.

Photograph: Courtesy Raised

5. Raised

Bars Cocktail bars Loop

Perhaps one of the most underrated rooftop bars in all of Chicago, Raised is often overlooked for its height (as so often is the case). But on the third floor of the Renaissance Chicago Downtown Hotel, guests get unobstructed river and skyline views that rival hot-shot rooftops nearby. 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.

6. Brando's Speakeasy

Bars Lounges Loop

True to form, Brando’s Speakeasy is anything but what it seems. It’s a lounge, but conversation flows more like a neighborhood haunt. The cocktail menus features interesting cocktails, like the Dolly Sister with gin, Aperol, strawberry purée, lemon juice, celery bitters and soda. The decor and vintage posters throw it back eras, but the karaoke and late-night dance music add modern flair.


7. Vol. 39

Bars Hotel bars Loop

You'll feel like a million bucks when you walk into the Kimpton Gray's loungey 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 nine different Old Fashioneds, several classic cocktails, six martinis and newfangled drinks, to boot. If you're feeling splurgy, order the Vol. 39 Vintage Old Fashioned with 30-year brandy, barrel-aged demerara sugar, angostura and orange bitters, and hand-carved ice. At $35, it's an investment, but it's totally worth it.

Chicago Riverwalk, City Winery
Photograph: Jaclyn Rivas

8. City Winery Chicago at the Riverwalk

Restaurants Mediterranean Loop

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.


9. Buddy Guy's Legends

Music Music venues Loop

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. You can usually catch a free acoustic show during lunch and dinner, or stop by later in the evening for a headlining set. 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.

The Game Room at the Chicago Athletic Association hotel serves cocktails from Paul McGee.
Photograph: Martha Williams

10. The Game Room

Bars Lounges Loop

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, accompanied by affordable, well-made drinks from Paul McGee (Lost Lake). 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.

Revival Food Hall bar
Photograph: Jaclyn Rivas

11. Revival Food Hall

Restaurants Food court Loop

You already love Revival Food Hall's lunch offerings, but did you know that the bar stays open till 9pm Monday through Friday? Saddle up for a classic cocktail, wines by the glass or beer—all of which are relatively affordable for the area. Save even more when you drop by for happy hour, available from 4 to 6pm daily: Select cocktails are $8 or $9, and bottles of wine go for $20–$25.

 2Twenty2 Tavern
Photograph: Courtesy 2Twenty2 Tavern

12. 2Twenty2 Tavern

Bars Gastropubs Loop

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 brussels sprout kabobs with bacon wrapped dates, Mexican Fire homemade chili and cheese curds, fried pickles & jalapeños with sriracha aiolo. Come for the giant Jenga and shuffleboard, stay for another drink.


13. Sky-Ride Tap

Bars Lounges Loop

Mosey through the swinging saloon-style doors at lunchtime and you’ll find polish sausages, hot dogs and chili being served to mustachioed laborers and Board of Trade employees alike. After work, it's an easy spot to grab a cheap beer (and maybe some dinner) before heading home.


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