Modern Bootleggers Deliver Cocktails Throughout Chicago

A stopgap measure to help pay the rent led a 31-year-old former events manager to create an illegal cocktail delivery operation that now employs seven people.

Bootleg Chicago started in March after this city resident watched her events business dry up when local stay-at-home orders went into effect. “It started with the pandemic,” says Sil, whose last name is withheld as her company is technically illegal. “I had an event with Nike, then they cancelled, and I was doing South by Southwest and Couchella, and nope, nope.”

Then, a driver totaled her car in an accident, and she had medical bills and other unexpected expenses that suddenly ate up her savings. “It put me in a weird position, like most of America is right now,” she says. “So, I quickly switched gears, and I said ‘What do I have on hand, and what can I do?’”

Sil knew how to make amazing drinks, and she had a bunch of liquors and juices leftover from previous events. “I also had these little pouches leftover from this event I was going to do,” she says. Those pouches looked like adult juice boxes,  and they contain the equivalent of two cocktails. With the help of another friend, a British woman who was stranded here during the pandemic because she wasn’t able to fly home,  she began mixing cocktails in an empty apartment building this friend was trying to rent out, and she posted on social media that they were available for delivery.

“I decided to call it Bootleg Chicago because it’s a modern day 20s thing,” she says. “We started making these cocktails, and I posted a one song, ‘Feeling Good,’ with me mixing them in black and white. People were intrigued, and the page was completely private, but we got a few orders.”

The first costumes she and her friend wore were Mexican luchadore masks with matching fur coats, and they delivered them with music.

The orders started small – just four a day – but with the masks, matching fur coats and music, the two of them delivered cocktails ina Jack Daniels cooler, and the delivery became an experience – like bringing a nightclub, for at least 15 minutes, to someone’s doorstep. “We started on March 18^th, and it was mostly friends who knew what I was doing, and they were trying to support me,” Sil says. “But after that, it took off like wild fire.”

Today, Sil employs seven people, donates part of her proceeds to nonprofits and needy people who live in her neighborhood. She and her team now deliver upwards of 150 cocktails a day, all over the Chicagoland area. Delivery is free, unless it’s out to the far-flung suburbs, and she offers a base menu of three drinks: the Feel Good, which is cucumber, tequila, agave, and chia seeds; the Remedy, which is a cold hot toddy with whiskey, honey, lemon and peach tea; and the Love Lockdown, which is vodka, and fresh raspberry lemonade.  The cocktails cost from $11 to $13, and add-on celebration packages cost a few dollars more.

Every week, she polls her customers about what kind of drinks they’d like to see on her menu. “Then, I have a rotating menu, and a few may stay on for a few weeks, or they might just be a special edition,” Sil says. “I also incorporate different (out of work) bartenders from around the city, and it’s called ‘Support Your Local Bartender’ initiative, which features their cocktails, and I give 100 percent of the proceeds to them.”

Her team also does birthdays, anniversaries and other celebration packages. She has a mini disco ball and sparklers, and she’ll also bring balloons. Besides the original luchadore masks, she and her team also will wear unicorn and panda masks.

“I had one man order a birthday package for his dad, and he teared up,” she says. “A woman also ordered a delivery package to the Ronald McDonald House for her sister, who’s son was in the ICU, and she was alone for her birthday.”

Even though her service is technically illegal, her team still checks I.D.’s to make sure that no one who is underage is being served, and she also is very careful about who she delivers to – new customers have to know someone before they can be added to her customer base. While Chicago recently allowed restaurants and bars to deliver cocktails, individuals who do not have establishments still cannot deliver cocktails.

“I know that it’s illegal, but I’m still doing something good, making people smile, and just taking people away for the moment,” she says. “I’m the modern woman version of Al Capone.”