Meet: Meg Daday

Founder

After practicing law for more than seven years, Meg Daday established Meg Chicago Real Estate in 2015 with the vision of helping busy professionals navigate the Chicagoland real estate market.

With a background as Associate General Counsel at a start-up, a fifth grade teacher in a low-income area and, possibly most importantly, as the oldest of six children, Meg intuitively took a consultative, educational, “older sister” approach to helping clients navigate the buying and selling processes.

After helping hundreds of families, establishing a series of community events for women and families, and building a collective of trusted collaborators, Meg Chicago has evolved to more than just Meg Daday.

A passion for interior design and a belief that everyone can create a home that they love prompted her to leave a thriving law career to help busy professional women and families meet their real estate goals. Over the last several years, she has helped over 250 women and families buy and sell in Chicago for more than $100M in sales volume.

Meg moved back to Chicago after graduating from Notre Dame Law School in 2007 and practiced commercial litigation for five years at firms in the Loop before serving as Associate General Counsel for the now-defunct Red Frog Events, formerly based in River North. Prior to law school, Meg taught fifth grade in Tucson, Arizona through Notre Dame’s Alliance for Catholic Education program. She graduated from Notre Dame with a Bachelor of Arts in American Studies in 2002.

FROM HERE TO HOME.

Meet: Sara Keller

Agent Partner

With over 9 years of experience in real estate and a background in Fine Arts, Sara brings a thoughtful, design-forward approach to every transaction. Originally from Shaker Heights, Ohio, she moved to Chicago in 2014 and now calls Old Town home. Purchasing her own home in 2021 deepened her passion for helping clients not only find the right space, but turn it into a place that truly fits their lifestyle. As the team’s boots on the ground, Sara is hands-on throughout the process - meeting with contractors, coordinating photo shoots, and overseeing the details that make a home shine. She specializes in creating seamless buying experiences with an eye toward both function and style. Outside of work, she loves spending time along the lakefront and enjoying her favorite neighborhood restaurant, Topo Gigio.

Meet: Mary Kate

Agent

As a mom of four young kids, elementary school speech teacher and now a licensed real estate agent, Mary Kate O'Brien is a Heyday Homes Associate Agent and the team’s boots-on-the-ground presence on the Northwest Suburbs.

On weekends, you can find Mary Kate and her husband wrangling their four young kids at baseball, soccer and swimming, volunteering at St Raymond's Church and School, joining a local running club or browsing the Mount Prospect Farmers' Market.

She loves introducing clients to the great communities in the Northwest Suburbs of Chicago and all that they have to offer for families, couples or dog-parents alike.

The Heyday Philosophy

Abstract icon of a chair next to a plant

1. personalized timelines for a personalized life

We champion those who refuse to put their dreams on hold for the perfect partner, plan, moment or milestone. Your goals define your timeline, not society's expectations.

2. curated, not calculated

We orchestrate opportunities with intention and authenticity. Every home showing, event, or connection is thoughtfully designed without the pressure of pushy sales tactics that still give us the ick.

3. room to grow

We celebrate expansion in all its forms: growing families, evolving careers, deepening friendships, and expanding perspectives. Life's richest moments happen when we give ourselves room to grow.

5. strategy meets soul

We blend data-driven market analysis with lifestyle intuition, ensuring every decision is both financially sound and emotionally aligned with who you're becoming.

4. intentional indulgence

We believe in saying yes to what serves you and no to what doesn't. Whether that’s selecting the right neighborhood, evolving your friend group, breaking societal standards or investing in experiences over excess.

 
 

Meet The Team

Meet Heyday Homes, a total home ownership team: your guide and support system, providing everything you need—real estate expertise, interior design advice and concierge-style services—to get from here to home and beyond. And when you make your next move, we’ll be right there with you.

Our expert team has a playbook and network of collaborators honed through years of real estate and design experience. Together, we create a tailored world of support that helps you take your life to the next level. We’re here to simplify each step and curate every detail, giving you room to focus on what truly matters.

your partner in all things home.