September 27, 2023 3:48 pm

A Bar For All Sports & Spirits Lovers in Chicago

Whiskey Girl Tavern

Actress/Comedian Lilly Singh once said “Women don’t need a seat at the table – we need a new table…. with enough room for everyone to bring our own chairs”.  This month we chatted with Heather Roberts, co-owner of the Whiskey Girl Tavern in Chicago who, along with her partner, Christina, decided that they needed a new bar, but a bar that embraced everyone. Committed to inclusion for all, they have created a welcoming space for people that are sports fans that love whiskey (and other spirits).

Heather’s early experience with whiskey was enjoying Derby Days when she was at Vanderbilt University in Nashville, first as an undergrad then a law school student. One of her fond memories from law school was a field trip to the Jack Daniel’s Distillery.

In 2013, she was hired to work in the legal department of Motorola after they were purchased by Google, and they moved her from California to Chicago. Finding herself in a new city where she didn’t know a lot of people, Heather accepted an invitation to join a flag football team, which was run by the CMSA (Chicago Metropolitan Sports Association), a not-for-profit sports organization that hosts both recreational and competitive play in athletic leagues throughout the year. Heather had been active in playing tackle football back in California and was looking forward to expanding her social network.

The day that she played her first flag football game for CMSA, the referee made a call that Heather didn’t agree with. Unbeknownst to Heather, that ref was Christina, who was filling in and was not only on the board of CMSA, but well known in the neighborhood for co-founding an annual festival that included a Whiskey, Wine and Women  event. According to Heather, Christina was initially thrown by the flack she was being given, but they ended up connecting and as she puts it, “the rest is history”.

Up until that point, Christina had been hosting events at different bars, bringing in revenue and Heather told her “You really need your own space to do these things.” At the time, Heather was traveling solo for her job. Each trip she would have dinner and drinks at the bar and take note of all the things she liked and didn’t like. 

When picking a bar concept, Heather and Christina’s shared love of sports was obvious, but they weren’t interested in opening “just a sports bar”. For their vibe, they chose a tavern. The tavern concept of a bar was Heather’s  favorite because the common denominator across all cultures in different countries she visited was the social factor. People of different backgrounds sharing sips and stories in taverns. One Fun random tavern fact Heather learned on a Boston tavern tour: the American Revolution was borne out of tavern conversations. And although sports is the main connector at Whiskey Girl Tavern, they wanted their drinks and spirits to be high quality without the pretentiousness.

Whiskey Girl Tavern’s bar program is curated by Meredith Barry, one of the twelve bartenders chosen to be on the Netflix show “Drink Masters” and competed for the title of “Ultimate Drink Master” and $100,000 USD prize. But Heather was already familiar with Meredith’s skill set since Meredith bar tended in their Andersonville neighborhood. She followed her career, becoming impressed with her combination of mixologist skills and people skills, so she enlisted her to create their bar program. 

Their staff is a combination of people Christina knew from when she was a bartender and people dedicated to providing a great experience, from servers that are looking to bartend and those that might work part-time.

Since their opening last year, Heather admits that the transition from consumer to bar owner has been eye-opening. The mechanics between running this type of business in addition to understanding spirits distribution, allocation (especially in the bourbon world), and the logic behind cost of a pour or drink are just a few of the presented challenges. 

She is grateful to be able to parlay her background in procurement towards running the bar, especially on the inventory side, and as someone with a minor in Computer Science, is a fan of using technology to help streamline their business. Her dream would be to have everything on one system and admits that one of her biggest pain points is being unable to integrate their systems.

Being able to follow the data of sales helps her to understand how best to serve her customers, whether it’s her regulars or hosted events in their space, from PTA Moms to birthday parties. And their data consistently shows that their number one seller across the board is their Old Fashioned.


They have over a dozen televisions throughout the bar to showcase women’s sports, however Heather reaffirmed that they are not aiming to be a “women sports only” bar. They’ve gone beyond the bar by supporting the local community through sponsorship of all the CMSA teams (since that’s what started it all) to sponsoring opening parties for other leagues.

Behind the bar, they support the education and growth of their staff through training and by example. When choosing the whiskey for their inventory, Heather goes above and beyond her love of bourbon, to keep up-to-date on other categories, by staying involved with tasting and inventory.

Heather’s Choice

Her favorite bourbons are Hancock’s Reserve from the Sazerac Company and Mayor Pingree Bourbon by Valentine Distilling in Michigan. For cocktails, she loves a good margarita or a Brooklyn (rye whiskey cocktail).

Christina’s Choice

When not enjoying their signature Old Fashioned, Christina sometimes drinks outside of the whiskey realm to enjoy an extra dirty martini with blue cheese olives.

When asked about what we can look forward to in 2023, Heather told me that their bar is in a constant state of evolution. When they first opened, they could only get an incidental license to sell liquor but eventually got a tavern license. Currently, they only have one bar in the front room with a catering bar in the back. There are plans for renovation of the back room where they will build a full-service bar, in addition to a beer garden and sidewalk café, for people to enjoy drinks outdoors in the summer months. 

The next time you’re in Chicago, Heather invites you to visit their bar in the Andersonville neighborhood to try their Old Fashioned!

"Whisky is liquid sunshine."

George Bernard Shaw

“The light music of whiskey falling into a glass – an agreeable interlude.”

James Joyce

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