Where Chicago's Most Successful Men Unwind with a Drink

By Shelby Livingston | September 30, 2016 | Food & Drink

Work is stressful, but a tasty cocktail can provide a much-needed respite after a busy day at the office. We were curious as to which watering holes Chicago's most successful men frequent, so we asked a few guys at the top of their game to tell us where they go and what they sip. Below, they spill on their favorite Chicago spots to unwind.

Scott Weiner, Co-owner of the Fifty/50 Restaurant Group: Oaxacan Sunset at Dos Urban Cantina

Scott Weiner.

“I love Dos Urban Cantina because of the people that work there and who treat the place like it's their home. Whenever I go, servers that have waited on me before in the dining room always stop by to say ‘hello’ and find out how I'm doing. When I bring friends, the warmth and hospitality that the staff shows my friends is just remarkable. I typically order a new cocktail every time I go there, but the most recent cocktail I enjoyed was the Oaxacan Sunset, which is a mezcal-based cocktail that reminds me of a Tequila Sunrise.” 2829 W. Armitage Ave., 773-661-6452

Jason Jared, Founder of Trifactive Sports Injury + Performance Clinic: Manhattan at Gather

Jason Jared.

“My favorite spot in the city is Gather. They make their Manhattan with Old Overholt Straight Rye, Carpano Antica, and brandied cherries. It's boozy and rich, with just the right amount of sweetness from the cherry. I get there a few times a week all year long.” 4539 N. Lincoln Ave., 773-506-9300

Todd Heiser, Principal and Design Director at Gensler: Mesa Verde at The Whistler

Todd Heiser.

“The Whistler. I love it because it’s one-part storefront art installation, one-part bar, and one-part music venue—and an absolute melting pot of culture. I have many fond memories of this place and love the rotating cocktail menu. My current favorite is the Mesa Verde: mezcal, triple sec, verdita, lime, and absinthe.” 2421 N. Milwaukee Ave., 773-227-3530

Rajan Sharma, Principal at Eon Clinics: Macallan 18 at Maple & Ash

Rajan Sharma.

“My go-to drink at Maple & Ash is Macallan 18, and I always have that with a splash of water. I then switch to wine and, depending on the time and day, it's either Merlot or Cab.” 8 W. Maple St., 312-944-8888

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