By Paulina Czupryna
Medill Reports
Tuesdays give dance instructor Jessica Mays a rare break from the endless loops of Ed Sheeran, Frank Sinatra and John Legend hits. She dedicates the other six days of the week to teaching 20- to 70-year-olds how to waltz to the song they choose for the most important performance of their lives — their first wedding dance.
The 44-year-old founder of Windy City Wedding Dance trains and competes around the world, one gown and graceful step at a time. Her company, named one of Yelp’s 100 best U.S. businesses in 2024, is Chicago’s go-to destination for wedding dance, Latin and ballroom lessons. Pedestrians may recognize her face postered on a window of the Fine Arts Building on Michigan Avenue, a historic arts hub since 1898 and the home of her business since its launch in 2014.
Mays recently expanded her work with Chicago Ballroom Studios, shifting her focus on social and competitive salsa, bachata and group classes that provide more opportunities for ballroom throughout the city. With an over 10-year business rooted in the city, The Knot put her dance lessons in its Hall of Fame. From first-dance preparation to group classes and a recent expansion, upgrades include 12 chandeliers, fresh furniture and new paint.
In 2008, when she moved to the city from her hometown in Fort Worth, Texas, a stroll on Michigan Avenue marked a serendipitous discovery. Stumbling upon a dance studio, Mays signed up for a small package of dance lessons.
She stepped out of her comfort zone by introducing the elegant world of ballroom into her repertoire, a direction she never intended to take before her move to the city. “It wasn’t drinking or sitting at a bar. It was simply a good activity,” Mays said.
When she played collegiate soccer at University of North Carolina at Charlotte and Marshall University, Mays often “knocked people over” and got rough on the field, she said. She brings that same “competitive” energy to the dance floor as a local and international competitor, winning first place at La Notte Delle Stella in Capri, Italy, and the Open Latin Championship.
“(Ballroom) pushed me,” she said. “It was a different side of myself that (I) hadn’t been in touch with.”
With her athletic drive, Mays said, “The first thing I did was sign up for a competition.”
After a few years of committing to the sport and its expenses, she said ballroom “got very expensive, very fast.” The intricately beaded and sequined gowns cost from $4,000 to $10,000. Mays took a six-month break and returned to her full-time corporate job at Smart Resources, a placement firm in 2010.
Over Christmas break that year, her brother encouraged her to return to dancing. Mays Google-ed Chicago dance studios and found Tommye Giacchino’s Ballroom University—a 16-week-long intensive training program through Chicago Dance. Within a week, she began classes. She trained under the Blackpool World Champion (a globally renowned dance competition), judge and renowned coach, and through Giacchino, Mays’ ballroom business began.
Giacchino, a recently retired Windy City Wedding Dance instructor, has more than 60 years of experience. When selecting the right employee, compatibility in work ethics was crucial for the expert. “When you’re working that closely with someone and you have them that many hours a week, you get to know someone quite well,” said Giacchino, who offered Mays the opportunity to manage her studio, Chicago Dance.
After five semesters studying new dance styles and two years managing a top studio, Mays formed a stronger bond with Giacchino. Along with tackling Chicago Dance’s marketing and management responsibilities, Mays also started a full-time job at U.S. Smokeless Tobacco. In 2013, Giacchino noticed a spot had opened in the building. “Jessica. This is your moment. This is the space,” she said over the phone.
Mays leapt at the chance. She returned to the Fine Arts Building, took a hand-operated elevator ride up the floors and asked the operator to take her to the leasing office. Coincidentally, the leasing manager was sharing the ride with her, overhearing her interest.
From there, Mays viewed her space and saw a future of potential. “I just need a wood floor. Is there a wood floor under this carpet?” she asked the manager. This marked the birth of Windy City Wedding Dance.
While the average length of a wedding dance is two minutes and 30 seconds, the average couple takes about 10 lessons preparing each twist, step and count of a choreographed routine. Foxtrot, rumba, nightclub two-step and salsa are some of the most popular dance styles. Mays stresses anyone can hit the dance floor.
From her updated website’s reviews, one couple mentions how “Jessica turned our ‘two left feet’ into a spectacular wedding dance.”
“I didn’t think I could ever really manage dancing,” immigration attorney Donald B. Kempster said. Before Mays, Kempster barely set foot on the dance floor. His serendipitous start to the practice began as preparation for his kids’ special day. With his practice only a block away from Mays’ studio, and two children with weddings in the same year, he invested in the practice about seven years ago.
Now, he competes as one of Mays’ partners, dancing in shows up to four times a year. When Kempster began splitting his time between Chicago and Spain, he invited Mays to visit his place abroad. Even while on vacation, Mays “was able to find a competition in the town,” he said. The dance duo’s organic commitment to the practice placed them in the 2024 Barcelona Crown Cup, taking home bronze.
“I thought I was gonna lose my lunch, I was so nervous,” Kempster said about his first competition with Mays. He said she eases the initial worry of confidently navigating the dance floor because she is “so patient.”
“No matter how bad you think you are, it’s something you can do,” Kempster said. He found ballroom checked every box of fitness, including “aerobic, balance, memory, improved rhythm and it gives you social opportunities.”
Ballroom is also a skill you “can use for the rest of your life,” he said. “I’ve met a bunch of people, and when you see yourself improving, you get a certain satisfaction from that.”
For Mays, “it’s the magic of the location.” With a Chicago studio, which is often a busier than a studio in the suburbs, the urban setting has been “super rewarding.” The city’s wide client access is helpful in getting “more people in one spot,” she said.
“Referrals are the most valuable leads,” Mays said. With more than a decade of one-on-one client services, and established partnerships with stylists, event planners and assistants, Mays’ referring clientele supercharges the studio’s growth. “I think this is the secret sauce.”
Mays is also a certified spray tan technician and owner of Spray Tans Chicago. When the pandemic halted the dance company, she needed ways to “maximize space and extra streams of revenue.”
“A spray tan business seemed like the answer,” she said.
Mays traveled to California for a week to get her certification at Sjolie, which provides multiple comprehensive courses on becoming a “sunless expert,” according to its website. Now, she spray tans herself and offers the option as an “add-on service” to the current client base.
In January, Mays and Stanislav Havrylchenko, performed at the 2025 Blissful Wishes Ball in January, Wish Upon a Wedding’s most anticipated event in the industry held at Morgan MFG. Wish Upon a Wedding’s mission focuses on granting weddings to couples facing terminal illness or life-altering health circumstances. Mays’ active participation strengthens her brand throughout the wedding arena.
When it comes to finding a partner, Mays only settles for the best. Along with Kempster, Havrylchenko has been Mays’ partner since 2022, and they debuted their first performance as a duo in 2023. Havrylchenko, who grew up in Ukraine, is an internationally trained professional who expertly balances a demanding dance career while raising a baby with his wife.
Havrylchenko dedicates time to the dance floor, fueled by Mays’ supportive training environment. He not only matches Mays’ rhythm but also devotes hours to training for events like the Chicago Austrian Ball, the Underground Private Party, the Black Nurses Chapter Ball and the South Shore Cultural Center’s showcase, with 10 more queued in his to-do. As a highly sought-after partner, he receives invitations to dance all over the world, including Italy, Poland and New York.
Along with the Blissful Wishes Ball, Windy City Wedding Dance supported the Chicago Junior League chapter at a benefit in March. Mays, who recently performed at the New York Dance Festival, is training for the West Loop Wedding Walk, a “wedding crawl” similar to a bar crawl but with buses that take couples to Chicago’s many wedding venues.
Mays also offers personalized father-daughter, mother-son, couples and group classes, and add-ons like bachelor party planning and last-minute dress tailoring
For any last-minute lessons, spray tans or social hobbies, Mays is the first to say, “I will” before a couple says, “I do.”
Paulina Czupryna is a magazine graduate student concentrating in data at Medill.
