Celebrating Leadership: Meet Chicago’s Female Entrepreneurs

In the dynamic heart of Chicago, a movement led by visionary women entrepreneurs is reshaping the city's business landscape. As we celebrate IWD 2024, we spotlight the city's female force, from the vibrant hospitality scene to the culturally rich museums and galleries. These leaders are not just running businesses; they're pioneering change and inspiring the next generation. Join us in celebrating the innovation, resilience, and solidarity of Chicago's most inspirational women, whose stories illuminate the path to a more inclusive and equitable future
Picture of Elizabeth Jenkins-Smalley

Elizabeth Jenkins-Smalley

Editor In Chief at The Executive Magazine

In the bustling metropolis of Chicago, a dynamic array of businesses flourishes under the stewardship of female entrepreneurs. This vibrant ecosystem encompasses a diverse range of sectors, from gastronomy and hospitality to culture and the arts, all underpinned by female ownership and management. As the world observes International Women’s Day in 2024, we turn our attention to a selection of Chicago’s most influential women in business, delving into their sources of inspiration and their endorsements of fellow female-owned enterprises within the city.

These trailblazers, through their innovation and leadership, contribute significantly to the economic vitality and cultural richness of Chicago. In their narratives, they not only share the motivations that drive their ventures but also spotlight their preferred women-led businesses, creating a network of mutual support and admiration. This feature aims to both celebrate and amplify the achievements of these remarkable entrepreneurs, whose efforts continue to shape the fabric of Chicago’s business community.

Amy and Clodagh Lawless

Owners of The Dearborn

Centrally located in the Chicago Loop, The Dearborn is owned by sisters Amy and Clodagh Lawless, who have years of expertise from working alongside their family in the business. In 1997, Amy, Clodagh and the rest of the Lawless family moved to the U.S. from Galway, Ireland, where they owned and operated several renowned bars, restaurants and hotels. The Dearborn is the first joint venture of Amy and Clodagh Lawless, uniting their passion for heart-felt service, a welcoming ambiance and classically rooted food that isn’t afraid to take culinary risks. Inspiration for the cuisine at The Dearborn starts with traditional American taverns, and from there Executive Chef Aaron Cuschieri taps into his passion for seasonal ingredients, farmers markets and contemporary culinary techniques to create dishes that lean towards the Midwest as well as those with a more global influence. 

What it means to be a woman in business/in your industry in Chicago:

Amy Lawless: “For me, being a women-run restaurant means we can create many wonderful opportunities to provide quality experiences for our customers and employees alike. With my sister as my business partner, we are proud to have created a very welcoming, diverse and accepting work environment. We are very attention-to-detail oriented and pride ourselves on top-class, genuine hospitality and service.” 

Clodagh Lawless: “Being the owner of The Dearborn, a women-owned restaurant, has taught me humility and perseverance. In a male dominated industry, I like to think that Amy and I have a strong foothold in the restaurant landscape of Chicago. This is due to our strong work ethic and more importantly, our love and passion for hospitality and our business.”

What inspires you?

Clodagh Lawless “Our incredible and dedicated team at The Dearborn are what inspire both of us everyday. Our success at The Dearborn lies in the fact that we surround ourselves with a team of talented people who are just as passionate about hospitality as we are.   There are also quite a few women in leadership at The Dearborn.  Our mission is to create the opportunity of a career path for all our female employees, from hourly employees to management level, that incorporates their many job roles in their lives.  It is simply unacceptable in the year 2024, that female employees need to bow out of the job pool to raise their families.  We aim to create a versatile and adaptable work week and environment, so that all of our employees can both work and spend time with their family.”

Amy Lawless “Our employees inspire us to be better leaders to those who contribute to the success of The Dearborn. In an industry where our team gives up their holidays, nights and weekends to provide an experience for our incredible guests, we try to give back to our work community as much as we can. Running a successful business is all about teamwork. Along with nurturing our wonderful team, the most rewarding part of owning our own restaurant is the daily opportunity to meet new people and welcome back our loyal regulars. We are part of their story now from once they enter our doors, and that is simply an honour!”

Theresa Nemetz

President of Chicago Food & City Tours

Theresa Nemetz launched her first tourism company in 2008 when combining her love of great food and travel adventures. Today, Chicago Food & City Tours features a team of itinerary planners ready to show off the hidden gems and delicious neighbourhoods of Chicago to local clients and tourists alike. Nemetz’s newest venture however looks beyond Chicago. Great Lakes Shore Excursions allows them to serve cruise lines entering the Great Lakes as well as offering group travel itineraries in 25 port cities on the Great Lakes beginning with Chicago and including other Great Lakes cities such as Cleveland, Detroit, Niagara Falls, Toronto ON, Sault Ste Marie, Mackinac Island, Duluth, Green Bay, Houghton and more.  Theresa proudly serves on the National Board of Director for the National Tour Association (NTA), also offers culinary vacations around the world under the name of Travel Deliciously, and someday looks forward to offering self-driving technology to tourism in Chicago.

What it means to be a woman in business/in your industry in Chicago:

“Not only in Chicago but across the globe, I appreciate that there is always collaboration at the forefront of the tourism industry. I believe this stems from women leading with compassion while serving as majority leadership in the tourism and service industries. We all rise together by promoting Chicago and each other’s businesses. I personally love being able to showcase so many great restaurants, iconic attractions, hidden gems and unique neighbourhoods in the itineraries that we craft for our clients. “

What inspires you?

“Every day, I have an opportunity to meet small business owners who are working together, promoting each other, and making their communities stronger.  I’m inspired every time we see a fabulous tour itinerary come together with facets from across the city to create a unique experience. From working with a corporate client to craft the perfect team outing, to planning a celebration event such as a bachelorette party or birthday dinner, we have made food the attraction.”

Hillary Marzec

Owner of Inside Chicago Walking Tours. 

Hillary Marzec is the founder of the #1-ranked tour business in Chicago (out of more than 400) on TripAdvisor, INSIDE CHICAGO WALKING TOURS. Having worked in Chicago tourism for more than 15 years, from boat tours to food tours to walking tours, she combines her years of experience as a teacher, writer, improv comedian, translator, tour guide, and product development specialist to create tours that tell the story of Chicago in a highly engaging, educational, and entertaining way. Hillary very much sees her work as a “calling,” often remarking that it brings her immense joy to be a part of enriching people’s experience of the everyday world around them, even if in a seemingly small way — “finding the extraordinary in the ordinary.” Her tours are so much more than “this building was created in 1924….”  They are a study of the world around us, making connections we might not readily make, and interpreting guests’ surroundings to add meaning and wonder to their experience of the world around them. She and her guides are all highly trained Chicago historians, theater performers, comedians, and teachers, and they are passionate not only about representing Chicago to visitors, but also about introducing locals to their own city through new, curious eyes. Celebrating her company’s 10th year of operation in 2024, she is proud that her WBE-certified small business not only survived COVID, but that it continues to thrive in an extremely competitive industry. When Hillary is not working, she enjoys walking around the city, swing dancing, cooking, traveling, and spending time with her friends, family, and — of course — her cats.

What it means to be a woman in business/in your industry in Chicago:

“Working in the tourism industry and teaching about all the great men who’ve designed and built the amazing buildings and structures around us, one can’t help but notice the distinct lack of women’s stories and voices. And so as a woman-owned small business in this industry, I feel like I’m somehow “leveling the playing field” in a way, guiding guests to experience this seemingly man-made environment through a woman’s eyes and perspective. It is extremely important to have a variety of voices telling our communal story and history: the telling of the story to interpret our surroundings and imbue them with meaning is almost as important as the creation of the surroundings in the first place. Storytelling — the act of interpreting our surroundings to provide meaning to what we see and experience — is part of what makes us human and connects us. I think that working in tourism the way I do allows me to add to, improve, and shape the narrative.”

What inspires you?

“I am inspired by people who are naturally curious, who live life with a wonder about the world around them — and I am inspired by people who discover that curiosity in themselves after having it buried or nearly snuffed out over the years. I am inspired by people who encourage expression in all its forms, and I’m inspired by people who eagerly listen to and validate others’ expression. I’m inspired by creative people, and by people who are able to add a little bit of their own angle to what we notice in the world around us. I’m also inspired by the goodness of people: selflessness, kindness, humility, consideration, generosity. The list goes on and on. In a perhaps very nerdy way, I’m also very inspired by things like math and space, and the intersection of science and beauty.”

Michelle Foik

Co-Owner of ERIS Brewery Cider House

Michelle Foik, 25 plus years in the Hospitality Industry, concentrating on Beer, Cider and Restaurants. Proud of being part of the Goose Island Brewery family for 10 years, followed into Revolution Brewing for 3 years. Started a journey with Cider at Virtue and Anthem Cider and became co-owner of the first women owned brewery and cider house – ERIS Brewing and Cider house. 

What it means to be a woman in business/in your industry in Chicago:

“Proud to be able to be respected in the Beer Industry for my knowledge, hard work, creativity and individuality by the men and women in the Chicago Beer industry.  To be in the industry this long and make it through all the challenges that everyone is facing was tough, but I am still here. “

What inspires you?

“The new generation of women and people that are making waves in the Chicago Craft Brew Scene.  When I first started there were a handful of women in our industry and recently, I was able to contribute to a collaboration brew with Charolette Converse (Solemn Oath) and over 80 women in the Chicago Beer Industry.  WOW I was so overwhelmed with happiness and power to see so many people in this day and age engaged with beer, cider and beverage in general.”

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