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The best downtown bars and nightlife in the Loop

From dives and lounges to rooftops and karaoke, here are the best downtown bars for drinking and music in the Loop

Photograph: Martha Williams
The Gage is one of the best downtown bars in the Loop.

The Loop is primarily a business district, which means that when 5pm rolls around, hordes of suits are heading for the train stations. The heart of Chicago is packed with more beautiful buildings than downtown bars and nightlife, but there are some solid leisure spots if you know where to look. Whether you're looking for a quick craft beer before heading home or a bit of jazz and karaoke, these are the Loop bars for blowing off some post-work steam.

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Downtown bars and nightlife in the Loop

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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Loop

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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Loop

Buddy Guy's Legends

If you want to see Guy perform at his own club, stop by in January when he takes over the schedules. If you show up the other 11 months of the year, you may well see him sitting at the bar, overseeing the whole operation: he’s more than just a name on the sign outside. There are acoustic blues sets on Fridays and Saturdays at 5:30pm. And if you like Louisiana cuisine, the kitchen has just what you need.

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Loop
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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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Loop

Jazz Showcase

Long heralded as Chicago’s leading jazz venue, the venerable club has been forced to relocate more than once since its inception in 1947. However, since moving to swank new digs in 2008, the Showcase has easily reestablished its reputation for bringing in top-shelf talent like the Bad Plus and Miguel Zenón.

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Downtown

Monk’s Pub

For more than 30 years, this cavernous Loop tavern has cornered the market on medieval dives. Beyond the heavy doors that seem to hide a monastery, you’ll find an after-work crowd of mostly suits and occasional skirts downing beer and adding to the piles of peanut shells littering the floor.

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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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Loop

ROOF

Recommended

TheWit Hotel’s swank 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. (Fireplaces and a glass enclosure mean it’s almost as packed in winter.)

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Loop

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 colorfully vested Board of Trade employees alike. After work, it's an easy spot to grab a cheap beer before heading home.

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Loop
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