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Underground Cocktail Delivery Service Thrives During Pandemic

As to-go cocktails remain illegal in Chicago, hustling entrepreneurs fill a need

A blue and white illustration of a woman delivering a cocktail to a customer while wearing a luchadores mask.
Underground cocktail services have thrived during the pandemic.
Illustration by Cori Lin

It’s Friday night and dance beats by reggaeton artist Bad Bunny are blaring on a speaker. Two women laugh while dancing with cocktails in their hands. They’re wearing blue latex gloves and they both have their faces covered: One wears a horse head, the other is sporting a Mexican luchador mask. But this scene isn’t playing out inside a club — it’s on a sidewalk. This is what getting an illegal cocktail delivered to your door in the age of the novel coronavirus looks like.

Restaurants and bars in Illinois cannot legally sell cocktails to go, though Gov. J.B. Pritzker said this week he’s ready to sign a bill to legalize them. Mayor Lori Lightfoot said Thursday Chicago will wait until mid-June to make them legal in the city. Cocktail kits, comprising ingredients that customers use to mix drinks at home, are permitted for delivery and carryout, but despite cries from the owners of cocktail bars, the Illinois Liquor Control Commission refused to grant them relief, leaving cocktail bars without a sorely needed revenue stream.

That’s led to services like Bootleg Chicago, which emerged with an Instagram account a day after the state closed all bars and dine-in restaurants on March 17. Its private account profile includes a description that reads “Must be 21+ to follow. DM for inquiries.” Once approved, users can message the account owner for details on how to place an order, and access 30 images hinting at the modern-day bootleggers’ identities.


Sil*, the creator of Bootleg Chicago, confirms this much about her identity: She’s a resident of Little Village on Chicago’s South Side and a freelance event producer. The week before the state’s stay-at-home order took effect, she saw lucrative event gigs disappear. First, SXSW canceled an out-of-town production. Then, Nike called off a sneaker release party where she was a hired vendor. Coachella fell next. Within a few days, all the events she depends on — including one with Chicago star Common — were put on hold or entirely off the table.

“My full income comes from festivals, parties, and concerts,” Sil says. “I kept asking myself, ‘What am I going to do?’”

For the last two years, Sil was a freelance event producer; a key part of her responsibilities was managing her client’s beverage program. A self-taught mixologist, she says she pays attention to the demographics of her clients and creates drinks based on their core tastes versus simply pushing product. Post-event, she analyzes data of attendees’ consumption and provides clients with report. Used to the fast pace of the entrepreneurial hustle, Sil suddenly found herself without a revenue stream to cover the cost of her rent, medical bills, and cellphone. She was trying to prevent herself from falling into what she describes as a dark mental hole when she decided to invoke the city’s bootlegging, Prohibition-era past.

Sil leaned on her experience producing experiential events, where her focus was more than serving up cocktails. She also wanted to provide an experience that left people feeling happy. Using surplus products she had at home from canceled events, Sil quickly launched Bootleg Chicago. Drinks are presented in clear zippered bags that resemble an IV drip.

Posts show an ingredient list heavy on Tajín and chamoy, a Mexican umami condiment made of pickled stone fruit. One of the few non-drink-related posts is a close-up of hands exchanging a bundle of tamales with the hashtag #SupportYourLocalTamaleLady. If there was any doubt the vendors behind this service are Mexican, it would be quashed upon closer inspection of the bar menu. The Como La Flor, a hibiscus-based cocktail, is a nod to a popular ballad by Mexican-American singer Selena Quintanilla, the first woman to win a Grammy in Tejano music. The drink is the color of a deep bruise, reminiscent of one of the singer’s most iconic looks — a sparkly purple jumpsuit worn during her performance at Houston’s Astrodome, the last before her untimely death. The michelada, a beer cocktail made with a variation of lime, salt, tomato juice, and/or Maggi sauce is common in Mexico and Mexican-American communities.

Sil does not shy away from this assumption about her cultural heritage: She says being Mexican absolutely plays a role in what she’s doing. It not only inspires her operations, it also acts as a sort of roadmap. She references Mexico’s street vendor culture, which has leaked across the border, as an example of how Mexicans will sell something as small as a packet of Chiclets to make a living.

“The devil works hard, but Mexicans work harder,” she says with a laugh.

Customers order from a list of options designed with wellness and good-for-you ingredients — Sil pays extra for produce from Del Dia in order to support local farmers. The Feel Good is made with chia seeds, cucumber, and lime. The Remedy is their version of a hot toddy, and Love Lockdown comes with lemon and raspberry. Three additional rotating drinks are offered weekly. There’s even an option to add on a chicken, pork, or vegetarian tamale for $2.50.

At launch, the business fulfilled three to four orders a day. The operations team consisted of Sil and Cris*, a Chicago local who now resides in Manchester, England, but who found herself stranded in her hometown because of COVID-19. In early April, she returned to the U.K. and launched a sister service. The drinks cost between $8 to $13 and are delivered for free across most of the city. Customers are given a timeframe of when their drink will arrive, but if they’re expecting a simple hand-off, this isn’t it. The bootlegger face mask of choice varies from Spider-Man to a panda bear head. They greet recipients with loud dance music, laughable moves to accompany the beats, and a cooler holding only what the person ordered.

For $25, customers can add on a celebration/birthday bottle service, which includes a song blast of choice, cupcakes, candles, a sparkler, and a personalized card. Visits last between five to 10 minutes, depending on how involved the receiving party is. Several customers have sent drinks to their loved ones to celebrate an important milestone, asking Sil to video-call them during the experience so they can be there. She says the neighbors don’t complain — in fact, many join the impromptu dance party and stick around for the brief laughs. Sil describes it as a moment where pent-up energy is released and everyone allows themselves to be free.

At publication time, Sil is completing 15 orders a day, averaging 75 to 100 drinks, and has hired a team to help fulfill demand.

“I don’t think I’ve ever worked this much in my life,” Sil says. “I went from not being able to pay my rent to being okay, and providing work for seven other individuals.”

By the second week, Sil needed to hire support staff to meet demand. The first hire was an operations/customer service rep who responds to inquiries, tracks daily expenses and sales, manages orders, and maps routes. Then came the driver, runner for store supplies, a production team working in an assembly line format to prepare drinks, and, of course, the performers who deliver the product.

The team buys what they need from grocery stores without stockpiling ingredients. They have also donated $1,200 to undocumented workers and the arts community, but not through a GoFundMe page or a nonprofit. Instead, Sil gives funds directly to people who have opened up about their struggles on social media and the street vendors she sees struggling to make a sale. For example, a father of two and former co-worker of Sil posted on Facebook his concern about not being able to provide for his family; she saw the post and gave him $200 in cash from Bootleg Chicago sales. When Sil walked past a candied nuts vendor outside of Atotonilco, the Mexican restaurant in Little Village, she gave him $50. Sil pops into virtual DJ sets to tip artists moving their performances online. She also engages out-of-work mixologists to create weekly specials where all the sales go directly to them.


Sil is aware of critics who remind her that what she is doing is illegal. However, she says the risk is worth the reward. Creating Bootleg Chicago gave her a sense of purpose and pulled her out of a state of depression. It gave her the opportunity to help others and bring joy back into people’s lives.

When the stay-at-home order ends, Sil says she wants to continue her mobile bar services, but do things the “the right way,” with a proper off-site liquor license. So far, the response has been overwhelming. Like most successful speakeasies, business growth has come from word of mouth rather than outright promotion. And while it may seem like the business model is focused on driving the sale of cocktails, Sil’s true success comes from giving people a reason to smile.

“People are getting married, graduating, and having birthdays,” she says. “These are once-in-a-lifetime milestones that should be celebrated, and this virus has taken it away. Even if it’s only five minutes that we’re celebrating that light, it’s worth it.”

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