By J.P. Anderson By J.P. Anderson | March 26, 2025 | Home & Real Estate, People, Feature, Features, Home & Real Estate, Featured, real estate, Home & Real Estate Feature,
Real estate power broker Dawn McKenna is creating a mini empire in Chicago and across the U.S., and she’s doing it the only way she knows how—by being 100% herself.
It’s something out of a fairy tale: South Side native marries high school sweetheart, raises four children and parlays a background in finance and a passion for interior design into a powerhouse real estate career. But that’s reality for Dawn McKenna, whose Dawn McKenna Group is at nearly $5.5 billion in sales and is ranked among the Wall Street Journal Real Trends’ top 20 U.S. real estate teams. As the fashion-forward Hinsdale-area resident builds her business and supports her 30-plus strong team, CS sat down with McKenna to get the scoop on her secrets to success, why athletes make great team members, and why she’s bullish on the state of the Chicago market.
Captured in her listing at 1248 W. George St., McKenna wears a Marchesa blush pink and mint green ostrich feather A-line strapless tea length gown from Mira Couture.
You’ve built the Dawn McKenna Group into one the top real estate teams in the U.S. Looking back, what helped you stand out and find your earliest success?
I think I was true to my authentic self. I was always into fashion and interior design, and my mother was into curating, collecting and architecture. On Sundays, we would go to open houses, and then we’d come home and reimagine our house. My dad was a school teacher; we didn’t have a ton of money, but I never knew it. And part of that was that it was instilled in me at a young age that putting your best foot forward does matter; focusing on the small things is your competitive advantage. People say “Don’t sweat the small things,” but if I had to say the single thing that catapulted me [to success], it would be that. I’m maniacal when it comes to details and making sure everything is just right for me, my team and the client. My first listing was through an acquaintance that was going through a hard time. This was my first week in real estate, and she called me and said, I know you don’t know what you’re doing, but I trust you because I know you will create a great experience. So creating an experience for somebody was my first dip into real estate. And I took that to the nth degree on that listing. I was the first one to do video. I was the first one to write a handwritten letter to the entire neighborhood inviting them for a sip and see to experience this house. I had macarons made with the address on the macaron. I loved the idea of creating something that people were better for having been there than before they came, and I staked my whole mission on that.
Photographed at The Palmolive Building, McKenna wears a Mira Couture custom magenta silk taffeta short dress with bow detail and off shoulder cape.
Now you have a team across six states. How important is that team to your success?
It’s everything. It is an incredible advantage I have in this world to have these people next to me. Basically, if you think about a force multiplier in combat or in the military—I’m not going to be so uncouth to say we are like soldiers—but at the end of the day, building a network [so] you can cast that wide net can only be done with team members that share your vision. I think my professional success, growth and happiness are completely tied up in my role as the founder and leader of the Dawn McKenna Group. When my team is successful, I’m successful. When they’re happy, I’m happy. That’s what makes a great team.
What makes a good Dawn McKenna Group agent?
They have to be sharp; they have to be ready to take on anything. They have to think before they speak, but also have the confidence to [say what’s on their mind]. They have to be able to be humbled or embarrassed and get back up and attack again. Some of the best team members I have are athletes. As a mom, all four of my kids were heavily involved in sports, [and I] stood in the stands and watched their tenacity and their ability to be good people and good team members. It’s the athlete thing that I think really sets us apart. Back in the ’80s and ’90s, investment banks hired basically all Ivy League and top 25 college athletes because, at the end of the day, they were willing to sacrifice, compete, and they were willing to put in the work consistently. That’s what I’m looking for.
Also at The Palmolive Building in a Mira Couture custom Champagne high-low strapless gown with velvet leaf patterned embroidery detail and crystal embellished sash, miracouture.com.
What are you’re seeing in the market right now?
If they’re priced properly, look better than the competition and are exposed to the market in a creative and strategic way, properties will be consumed because it’s what the market craves. I think overall, there’s a state of cautious excitement. Our clients are very bullish and ready to find their next dream home, and I think there’s a lot of pent-up [desire from] buyers out there who were waiting to time the market and time the interest rates. I will tell you that Chicago came out with a bang this year—we had 20-plus transactions in the first three to four weeks of the year. It was a wild January, which is surprising, and that says a lot. People want what they want.
What keeps you passionate about what you’re doing?
There’s nothing that beats the joy that a new home brings a family, a young couple, a single person that made some money and now is investing. I’m focused now on trying to do more sophisticated things on LinkedIn and social media; we created an industry-changing technology which we wound up selling to one of the biggest names in PropTech out of California, and I’m anxious to build off that. The creative marketing, the memorable events ...we can change the way business is done, and we have. So I’m excited about that new innovation and the evolution of what’s to come.
Where do you hope to see DMG in five years?
This is a majority women team, and I really enjoy working with young women and girls outside of real estate as well and being an inspiration for them. I tell my team all the time, if you want to be married, have a family and have a career, you can do it all. It’s not without sacrifice and people at your side to help you through the good times and the bad. [Aside from that,] I would like to have some type of impact not just in real estate numbers, but in the industry-changing technology and events we have that bring people together. So in five years, I want DMG to be more [tech-forward], more creative and more successful, while also not losing passion, the personal touch, the hard work and that client-first attitude. I mean it—always, always, always, no matter what, the client is first.
Photography by: KATRINA WITTKAMP