Planning with heart, structure, and a whole lot of calm.
A steady presence for one of life’s biggest moments.
You don’t need to do it all, you just need the right support.
Planning a wedding is exciting, meaningful, and, let’s be honest, a lot. Between timelines, vendor communication, budgets, and the emotional weight of bringing families together, it’s easy for the joy to get buried under logistics.
At Ashlee Stapleton Events, we believe couples deserve to feel relaxed, confident, and fully present on their wedding day. Our role is to manage the details, protect your peace, and create a planning experience that feels collaborative, steady, and supportive from start to finish.
Our Story
Hi, I’m Ashlee and this work found me for a reason.
I’m the founder and lead planner of Ashlee Stapleton Events, based in Chicago and the surrounding suburbs. I live here with my husband of five years (together for fifteen) and our two dogs that we’re completely obsessed with.
My journey into wedding planning began with my own wedding, or rather, the version of it that didn’t go as planned. As a COVID bride, I had to let go of parts of the day I had envisioned, and I was left with a feeling of unfinished work. Instead of letting that experience harden me, it sparked something deeper.
I started channeling that energy into hosting events for the people I love: Galentine’s Days, Friendsgivings, birthdays, showers, and engagement parties and I quickly realized that what stressed others out actually filled my cup. Planning felt natural, joyful, and purposeful.
That realization led me to leave my corporate career and build a business rooted in care, intention, and calm so other couples wouldn’t have to carry the weight alone.
Where heart meets structure.
Planning a wedding is essentially managing a months-long (sometimes years-long) project with budgets, timelines, contracts, people, and emotions all happening at once.
With over eight years of professional project management experience, plus firsthand experience planning weddings and countless celebrations, I bring both structure and empathy to every event. I’m deeply organized, detail-driven, and proactive but just as importantly, I know when to steady the room, simplify decisions, and remind you what truly matters.
It isn’t about perfection. It’s about flow, intention, and trust.
Calm, collaborative, and always in your corner.
Our planning approach starts with collaboration; we’re in this together. You can expect transparent communication, honest guidance, and a steady presence when things feel overwhelming.
I believe in being hands-on, thoughtful, and proactive anticipating needs before they become stressors and solving problems quietly behind the scenes. When questions come up, deadlines approach, or emotions run high, I remain calm and clear so you can do the same.
The goal is simple: when your wedding day arrives, you’re laughing with your favorite people, sipping a drink, and soaking in the joy, not answering questions or managing timelines.
When I’m not planning weddings or events, you’ll probably find me:
Cooking in my kitchen with a glass of wine nearby
Ordering an old fashioned or an extra dirty martini
Rewatching comfort shows like Friends, The Office, Parks & Rec, and Modern Family
Traveling (Boston has my heart, it’s where we got engaged)
In more than one fantasy football league (and managing them quite well)
Cuddled up with my husband and our dogs
While I take this work seriously, I believe the best planning relationships are built on trust, warmth, and genuine human connection. Whether we have differences or commonalities, my goal is to build personal connection and trust.
A little more about me, because connection matters.
If this feels like your kind of planning experience, let’s talk.
You don’t need to have everything figured out. You just need someone who can guide the process, manage the details, and support you with confidence and care.
Ashlee Stapleton Events proudly plans weddings and lifestyle events throughout Chicago and the surrounding suburbs, serving couples who value intention, collaboration, and a stress-free experience.