Chicago’s best bar for . . .

Professional networking

RL Restaurant

If the walls could talk, plenty would listen. RL means business, from its impeccably dressed clientele and crisp white tablecloths to its country-club cuisine and service. Portraits of historic movers and shakers line the wood-paneled walls while those in its buttery leather booths are making significant deals of their own.

A team happy hour

Roanoke

Early on most every weeknight evening, you’ll find the U-shaped bar at this casual Loop spot filled with savvy imbibers. Happy hour is a sport here, and Roanoke always has its game face on. A 12-top communal table in the handsome, dark wood-filled space is perfect for your after-work gang.

Celebrating a company win

Asador Bastian

You can tell a lot about a place just from its napkins and knives, which here are plush and monogrammed, respectively. Located inside a multistoried historic townhouse, this Basque-influenced steakhouse and its dapper first-floor lounge quietly exude class, from its vintage cocktail list to aged steaks from rare specialty cows.

Getting inspired

Dearly Beloved

Tarantula tincture, liquid chlorophyll, ube pineapple air—this cutting-edge River North bar nudges customers out of their comfort zones with eye-catching cocktails. Stuck on a solution for a new campaign? The chill vibe and Instagram-worthy drinks—a mascarpone-infused espresso martini, perhaps—might be just the ticket to inspire some out-of-the-box thinking.

Showing off stellar views to a client

Z Bar

It’s not the highest rooftop bar in the city but what this sophisticated Peninsula Chicago hotel lounge lacks in altitude it more than makes up for in attitude. Whether you sit at the oval-shaped bar, low-top tables, or casually chic patio, dramatic views of Chicago’s iconic skyscrapers will surround you. 

Confidential conversation

Pearl Club

Need to seal a top-secret deal? The only connection to the outside world at this intimate lounge is its revolving door. Inside the triangle-shaped space are jewel-toned couches and cozy nooks with glam light fixtures providing a warm glow no matter the time of day. Sit back and relax; no one is watching.

Sipping alfresco

The Bellevue

Hiding in plain sight in the heart of the bustling Gold Coast, this modern American restaurant and lounge feels like an insider’s secret. The expansive plant-filled patio is a prime people-watching perch that more than lives up to its name—beautiful view. It’s a little slice of paradise under the sun or stars.

A nightcap after a business event

Maple & Ash

This multistory steakhouse has swagger to spare and doesn’t hold back when it comes to lavish extras. Nor should you. Plush velvet chairs, wood-paneled ceiling, and luxe light fixtures add to its celebratory vibe. A special nightcap menu features a mini espresso martini tree and caviar and champagne service.

Photography by Lyndon French