The best downtown bars and nightlife in the Loop

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

Photograph: Jordan Avery

The Loop may be the center of commerce in Chicago, but when 5pm rolls around, you'll find workers flocking to dives, rooftops and cocktail lounges in the area. You can join the suits over a craft beer at a gastropub with TVs lining the walls or head to one of Chicago's best blues clubs for a late night show. Don't settle for a boring night of drinking downtown—dig into our guide to the best bars and nightlife destinations in the Loop.

RECOMMENDED: Our complete neighborhood guide to the Chicago Loop

Best bars and nightlife in the Loop

1

Monk’s Pub

For more than 30 years, 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.

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2

Cindy's

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 drinks from Nandini Khaund and seafood platters or charcuterie boards designed for sharing with a group. Just make sure you have a reservation—the wait to get on top of this hotel can drag on for hours.

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3

The Berghoff

The legendary, century-old German haunt has added a few modern dishes to the menu over recent years (bacon-wrapped shrimp, molasses-crusted 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.

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4

Vol. 39

The Kimpton Grey's lounge area, Vol. 39 shows off a library-like feel with leather chairs in a modern setting. Sit back and relax with cocktails from Jess Lambert and bar snacks from chef Brian Millman. If you really want to feel fancy, peruse the list of rare wines and order from the caviar cart.

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5

Buddy Guy's Legends

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.

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6

The Game Room

Recommended

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.

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7

The Revival Food Hall

You already know that Revival Food Hall is a great place to grab some Furious Spoon ramen or Smoque barbecue, but you can also sit down at the hall's bar and get a decent drink. Bartenders offer a selection of basic cocktails (French 75, Singapore Sling), a small menu of draft beer and plenty of bottled or canned options. We won't judge you if you need a stiff drink on your lunch break, but the bar is open until 9pm on weekdays so you can also swing by after work.

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8

The Gage

Recommended

The best after-work bars have something for everyone—a strong beer list, well-made cocktails and wines by the glass. The Gage offers all of these, as well as great bar snacks. Order Scotch eggs, PBR-battered fried pickles and pork shoulder poutine to soak up the booze and ensure you won’t be hungover for work the next day.

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9

2Twenty2 Tavern

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.

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10

City Social

Why it's taken this long for an upscale bar to take up residence mere steps away from City Hall is beyond us, but City Social Kitchen and Bar is clearly the kind of place that this area of the Loop has long demanded. Walk by during the week, and you'll find it packed with young (and older) professionals enjoying cocktails, 20 draft beers and televised sports. The menu offers a cross between classic bar fare (burgers, wings, guacamole), Italian dishes (pasta, linguini with clams) and seafood (including a poke bowl).

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11

ROOF

Recommended

TheWit Hotel’s swanky rooftop lounge sports a specialty cocktail menu, a well-curated wine list and small plates, but it’s the breezy terrace-with-a-view that draws crowds, all ready to throw elbows to score tables per the seat-yourself policy. Stop by to enjoy the views or to catch a movie during the TheWit's screening series. Fireplaces and a glass enclosure mean it’s almost as packed in winter, so don't let a little snow stop you from getting on the ROOF.

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12

Brando's Speakeasy

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 mashups like a Rosemary Maple Bourbon Sour and Strawberry Ginger. The decor and vintage posters throw it back eras, but the karaoke and late-night dance music add modern flair. While it’s not as Don Vito Corleone meets Al Capone as the name might imply, Brando’s is definitely a mash-up.

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13

The Plymouth Restaurant

The man behind White Palace Grill and Hollywood Grill is behind this affordable Loop diner stocked with a full bar and a menu of munchies, hot sandwiches and breakfast served all day. And since it’s not every day you come across a rooftop deck in the middle of the Loop, we recommend taking it upstairs if weather permits for an after-work drink.

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14

Sky Ride Tap

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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