Meet a Mom: The Motherhood Journey with Kelly and Jenny of The Mama League North Shore

Hello friendly faces! It’s a new Chicago North Shore Moms spotlight brought to you in part by Mary Gifford of Gifford Law.

Navigating motherhood is an incredible journey, but it’s even better with a supportive village by your side. That’s exactly what sisters Kelly and Jenny set out to create with The Mama League North Shore, a community where new moms can find expert guidance, real connections, and a judgment-free space to grow together.

With backgrounds in education and behavioral health, these two North Shore moms know firsthand how overwhelming early motherhood can be. After having their sons just six weeks apart, they realized a crucial need for more in-person support and resources for moms in the area. Now, they’re bringing high-quality education, newborn classes, CPR training, and fun events to moms across the North Shore. How great is that?!

Learn more about Kelly and Jenny’s own motherhood journey, their favorite local spots, and how The Mama League North Shore is helping moms thrive.

Hi Kelly and Jenny! Please introduce yourself. Where are you from originally? What city do you live in now? What brought you here?

Kelly:
We’re sisters who grew up in the Northwest Suburbs and have always been close. After college, we both lived in Chicago, embracing city life. Most recently, Jenny and her husband were living in San Francisco, but when she found out she was expecting (just six weeks behind me) it became clear that moving back home to be near family was the right choice. And while I love the city, the prospect of more space, the lake still nearby and top-rated schools made the North Shore a natural next step with a baby on the way. We now call Northbrook home, while Jenny lives just five minutes away in Deerfield!

Jenny, Matt, and baby Theo

Tell us about your children.

Jenny:
Our boys are just six weeks apart. Cooper, Kelly’s son, is 10.5 months old, and my son Theo is 9 months. Despite us being so alike as sisters, our little ones couldn’t be more different! Cooper is bursting with energy and constantly on the move, while Theo is a social butterfly who loves observing the world around him.

Kelly, Brad, and baby Cooper

What are one or two fun facts, and/or important things to know about you?

Kelly:
Jenny and I were born just 18 months apart, and we’ve always shared a close bond and a lifelong dream of working together. After spending a decade in parallel careers, we knew it was time to join forces.

With master’s degrees in education, we’re deeply passionate about providing high-quality education to moms. My background includes working as a special education teacher and instructional coach at an alternative high school in the suburbs, while Jenny began her career in behavioral health at Lurie Children’s Hospital before transitioning into special education. She later became an administrator at an independent school in San Francisco. Now, we’re combining our expertise to make a meaningful impact together!

What are your favorite North Shore places, spaces and eats to frequent?

Jenny:
I love taking Theo to the Deerfield Library; he’s working diligently through the reading “1,000 books before kindergarten” program 😅.

Kelly has spent many days walking Cooper at The Chicago Botanic Gardens and relaxing at Rosewood Beach.

Our regular go-to restaurants for takeout are: Three Tarts Cafe in Northfield, and Taco Vida and Jimmy Thai in Deerfield.

For a more upscale night, we enjoy taking the boys to House 406 in Northbrook or any of the Ballyhoo restaurants as they are always so family friendly and accommodating! DeNucci’s in Highland Park transports us back to our city days!

Love your recs! Any good reads or TV viewing we should check out?

Kelly on books:
Right now, we’re diving into Good Inside by Dr. Becky Kennedy because our boys are growing up fast, and we want to stay ahead on parenting strategies! For fun, I’m engrossed in The Women by Kristin Hannah, while Jenny is savoring The Goldfinch by Donna Tartt.

Jenny on the what to watch:
On the screen, Kelly just wrapped up Paradise, and I am reminiscing about my post-grad travels in Thailand while watching The White Lotus. And for a little comic relief, we’re rewatching Modern Family, which definitely hits differently now that we’re parents!

What’s one piece of motherhood advice you’ve gotten that’s guided you?

Jenny:
When I was just two weeks postpartum, an experienced mom shared a simple yet powerful piece of advice: “Get out of the house, even if you don’t think you need to.” That gentle push led me to join a Newborn Series cohort in Hinsdale, where I realized the incredible power of community in motherhood.

Despite having boys just six weeks apart, we both felt how isolating and overwhelming early motherhood can be. That experience sparked the idea for The Mama League, a space where moms on the North Shore can find their tribe, share laughter (and tears), and navigate all of motherhood’s ups and downs together. Every mom deserves that kind of support, and we’re here to make it happen!

And speaking of motherhood, isolation and tribes, tell us more about The Mama League North Shore.

Kelly:
As two Type A women, we thought we had done all the research we needed before having our boys. Growing up, we watched our mom raise three kids in four years, making motherhood look effortless. But once we became moms ourselves, we quickly realized just how challenging (and overwhelming) it can be. On top of that, we were unprepared for the sheer volume of often-times conflicting information flooding our social media feeds.

That’s what inspired us to create The Mama League North Shore; a community built to provide moms with real, reliable support and education, without the noise and pressure of the internet. We offer Newborn Series classes, CPR and anti-choking classes, as well as mom’s night outs and other fun events!

What’s The Mama League mantra?

Empowering and educating moms, growing together with expert guidance, genuine connection, and a thriving community of support.

What classes do you have coming up that you want our readers to know about?

Our Newborn Series has a cohort starting on April 30th for moms with babies ages 0-4 months. This eight-week series brings in local experts to cover essential topics like feeding, sleep, postpartum recovery, baby’s physical therapy, maternal mental health, and travel. The classes are intimate and held at Kelly’s house, so moms don’t have to worry about germs in a public setting. Plus, the relaxed environment allows moms to move around and tend to their babies as needed while still fully engaging in class.

We’re here to help moms build their village, and by grouping the cohorts by birthdate, it gives moms a chance to connect and form friendships with other moms that are in the exact same phase of motherhood that they are. We’re also hosting an Infant and Child CPR Class on April 24th at Bubbles Academy in Highland Park. For those looking for a more personalized option, we offer private, in-home CPR classes—perfect for parents who want to gather friends for an educational night or for families who need grandparents, nannies, and caregivers to learn these lifesaving skills. Our goal is to help everyone feel confident and prepared in an emergency.

Registration for these events can be found on our website: https://themamaleague.com

Do you host mommy meet ups?

Yes! We have a Moms Night Out Event coming up on May 1st from 6-7:30 pm at Bashy Bash in Winnetka. Babs Boards will be leading a charcuterie board making class and wine will be served!

We also have meetups for moms with older kids and moms night out events in the works. Follow us on Instagram (@mamaleaguenorthshore) for more updates!

Do you collaborate with local businesses?

We’re always looking for new partnerships, whether it’s sponsoring a Mom’s Night Out, hosting a weekend meetup, or supporting other community events for local moms. If you’re a business interested in partnering with us, we’d love to connect! Reach out to us at [email protected].

Why did you both decide to start the North Shore branch of The Mama League?

Kelly:
When Jenny’s son was born, she was living in Hinsdale and, after an especially rough postpartum night, signed up for a Newborn Series class. After just one week of class, she called me and said, “We need to find something like this on the North Shore.”

At the time, there weren’t any Mommy & Me classes in the area that combined expert guidance with a strong sense of community. The next step was obvious; we needed to bring The Mama League to the North Shore to provide valuable resources and support to local moms.

Is there anything else you’d like us to know about The Mama League?

Jenny:
While our Instagram may look polished and pretty, The Mama League is all about showing up exactly as you are. In our Newborn Series, there’s no pressure to have your hair or makeup done—unless that makes you feel good, in which case, go for it! But if your big win for the day is simply getting yourself and your baby out the door (somewhat) on time, that’s just as amazing.

Kelly:
We also have gift cards available, which are perfect for Mother’s Day or baby showers!

Our goal for every class and event is simple: to create a space where moms can laugh, commiserate, and genuinely enjoy time together. Motherhood is a wild ride, but you don’t have to go it alone. We hope to help you find your tribe – join us at our events!