This week’s Chicago North Shore Moms‘ Small Business Spotlight features the incredibly thoughtful and community-driven Jessica Ortega, founder of Giggles, a Reggio-inspired indoor playspace located in the heart of Highwood, IL. Originally from the Philippines and raised in Virginia Beach, VA, Jess made her way to the North Shore in 2016 and quickly fell in love with Highwood’s charm and sense of community. Jess’ background as a nanny and preschool teacher, combined with her tried and true experience in flexible and functional play spaces, Jess created Giggles as a calm, creative haven for kids and their grownups. Whether she’s welcoming families at Giggles or stepping into her new role as President of Celebrate Highwood, Jess is all about building spaces where people feel connected, supported, and inspired. We are so thrilled to spotlight you, Jess!
Photo credit: Katie Michelle Studios
Hi Jess! Please introduce yourself. Where are you from originally? What city do you live in now? What brought you here?
Hi! I’m Jessica Ortega, Jess for short. I was born in the Philippines and grew up in Virginia Beach, VA. My dad was in the Navy, so we were lucky he was stationed in Virginia for most of my childhood. In 2016, he was at Naval Station Great Lakes and asked if I’d consider moving to Illinois. I said sure, packed up my little car, and just…went. I bounced around Chicagoland for a while before settling in Highwood in 2021. From the moment we got here, my fiancé and I knew we were staying. It just felt right.
What are one or two fun facts to know about you?
During the pandemic, I got really into the video game, Animal Crossing. I ended up streaming on Twitch, making YouTube videos, and connecting with people from all over. What started as something fun to do turned into real friendships and a strong reminder of how powerful having a community can be (even in a virtual world).
Another fun fact? I had almost every kind of pet growing up. Dogs, snakes, lizards, fish, birds…you name it. The only thing I didn’t have was cats. Now I have two. We adopted Kanga and Roo (named after the Winnie the Pooh characters) in 2017.
Adorable! Besides Giggles, of course, what are your favorite North Shore spots?
I am a Highwoodian through and through, so most of my favorite spots are right here in town. And, if you know me, you know I love food so Highwood is pretty much perfect.
Da Local Boy – This Hawaiian fusion spot (owned by fellow Filipinos!) is absolutely delicious. Their food feels like going home and having your lola (grandma in Tagalog) cook for you: comforting, flavorful, and made with love.
La Plancha Loca – I’m there almost every Tuesday for Taco Tuesday. The Plancha shrimp tacos are my go-to. Their new cantina is such a great place to spend time with friends.
When I want to slow down a little, I head to the lake. Fort Sheridan and Openlands are my two favorite spots. It’s definitely not the ocean (spoken like a true East Coast transplant), but it can be absolutely breathtaking.
Any good reads you’d recommend?
I recently finished Let Them Theory by Mel Robbins. I even attended her book tour stop in Chicago and got to meet her. I love books that make me think about how we move through the world, especially when it comes to leadership, creativity, and community.
Speaking of inspired minds, what’s your mantra?
If I had to sum it up, it’s this: be the person you needed when you were younger.
My family always taught me the importance of showing up for others, even when there’s nothing in it for you. Growing up in a military family, my parents would “adopt” single soldiers who were stationed far from home. They’d come over for holidays or Sunday dinners, and for a while, they just became part of our family.
At the time, I didn’t realize how much that shaped me. But now, whether it’s through my business, friendships, or community work, I try to create that same kind of belonging wherever I go.
I think that is the very essence of who you are and why Giggles is such a special place. So, tell us more about Giggles indoor playspace! What is it and what makes this play space so unique?
Giggles is a Reggio-inspired indoor playspace, which is just a way of saying it’s designed for open-ended, child-led play. Nothing’s flashy or overdone; every corner is set up to inspire curiosity and connection.
I always say we’re not your average playplace. Littles lead the way here, and we follow. It’s creative, calm, and built to give families a chance to slow down and just be.
Photo credit: Katie Michelle Studios
Do you have an educational background?
I was a nanny and preschool teacher for years, and I’ve always been drawn to creative environments that give kids freedom to explore. Most of what I’ve built with Giggles has come from real experience and a lot of paying attention to what actually works for kids and families.
Photo credit: Erin Loughlin
What was the impetus behind opening up this indoor playspace?
Honestly, I just couldn’t find a space like this when I was a nanny. Everything was either overstimulating or overly structured. I wanted something more open, more thoughtful. A place where kids could follow their own curiosity and where parents didn’t feel rushed or out of place.
Photo credit: Katie Michelle Studios
It’s your 2 year anniversary – how are you celebrating?
We’re taking a break from our Jubilee this year but will bring it back next year! Right now, I’m just taking a moment to reflect. Two years of Giggles is two years of laughter, learning, and community. That alone feels worth celebrating. Plus, we will be taking some time off to celebrate my own birthday (I am turning 30!) with family and friends.
It takes a village – is there anyone or any group in the community that has been instrumental in the success of Giggles?
The families who show up. Giggles is what it is because of the parents and caregivers who believe in play as much as I do. Also, my Highwood community—local businesses, friends, and even the city itself—has been incredibly supportive.
You’re also the incoming president for Celebrate Highwood. Tell us about Celebrate Highwood and what your role entails. What enhancement do you forecast for the future?
Celebrate Highwood is the nonprofit that puts on all the big events in Highwood: Pumpkin Fest, the Wednesday Market, Nashwood, and many more. I’m stepping in as the new president this year to help shape the vision and keep things moving.
My focus is on making sure we’re planning with intention and building strong local partnerships. And if you’ve ever wanted to be more involved in town, this is your sign. Come volunteer, help with an event, or just share your ideas – we’d love to have you!
Picture above: Jess and her family volunteering for Celebrate Highwood’s Annual Pumpkin Fest.
What’s on the horizon for Giggles?
We’re continuing our Parents’ Night Out events since they’ve been such a hit. Kids have a great time, and parents get a well-deserved break. We’re also rolling out outdoor music classes this season, which I’m really excited about.
We’re always thinking up new ways to serve our community. Whether it’s a pop-up event or something playful we haven’t tried yet, we love keeping things fresh. You can always check our website or newsletter to see what’s coming. There’s a lot in the works, and we’re just getting started.
What else would you like our readers to know about Giggles that we didn’t cover?
Giggles is more than just a playspace. We host open play, classes, birthday parties, and events—all designed to keep things creative, playful, and welcoming for both kids and grown-ups.
Summer tends to be a slower season for indoor spots like ours, so if you’ve been thinking about stopping by, now’s a great time. Whether you come for a play session, book a party, or join a class, it really makes a difference.
We’d love to see you sometime soon.
Give us your deets!
Giggles is located at 328 Green Bay Road, Highwood, IL. You can reach us at 847-748-8621. Check out the inspired fun on our Instagram: @giggles.play
More from Chicago North Shore Moms:
Small Business Spotlight: Backyard Dreams Built Here: Meet Jake from Fenceworks
Carly Ubersox on “Honey-Do” to Done: How Honey Homes Simplified My Home Repairs
Small Business Spotlight: Growing Leaps & Bounds with Aneri Bhansali, PT, DPT
