Courtney and Matt’s Chicago wedding was a beautiful reflection of their warmth, deep connection, and genuine kindness. After photographing their engagement session nearly a year ago, I knew their day would be something extraordinary. Courtney, a dedicated grade school teacher, and Matt, a driven lawyer, met over a game of bocce ball — but their […]

A Modern Chicago Love Story | Courtney & Matt

weddings

Courtney and Matt’s Chicago wedding was a beautiful reflection of their warmth, deep connection, and genuine kindness. After photographing their engagement session nearly a year ago, I knew their day would be something extraordinary.

Courtney, a dedicated grade school teacher, and Matt, a driven lawyer, met over a game of bocce ball — but their history is even more layered than that. They attended the same school and shared social circles for years, somehow never meeting until fate stepped in to connect them.

Getting Ready

The day began with Courtney and Matt surrounded by their closest friends and family, getting ready for the moments that would change their lives forever. There was so much excitement in the air as Courtney slipped into her gown, helped by her bridesmaids and her mom.

Meanwhile, Matt and his groomsmen shared a few laughs while getting suited up, exchanging stories and preparing for an emotional first look.

Portraits

Before the ceremony, Courtney and Matt shared a first look that was absolutely heart-melting. The emotion and relief on their faces said it all — the day they had been dreaming of was finally here.

We captured portraits with their phenomenal wedding party, whose support and energy added so much to the day. Every smile, every hug, and every joyful cheer from their closest people made these portraits truly unforgettable.

The Ceremony

Their ceremony at Fairlie was heartfelt and deeply meaningful. Loved ones gathered as Courtney and Matt exchanged vows that reflected their respect, devotion, and shared dreams. There wasn’t a dry eye in the room as they promised each other a lifetime of love.

Emotional wedding ceremony in Chicago
Emotional wedding ceremony in Chicago
Emotional wedding ceremony in Chicago
Emotional wedding ceremony in Chicago

Reception Highlights

The celebration continued with a lively reception featuring heartfelt speeches from family and friends, an epic first dance, and a high-energy live band that kept the dance floor packed.

Courtney and Matt ended their night on a deliciously fun note with a food truck from Cheesy — the perfect late-night bite for guests who couldn’t stop celebrating.

It was an honor to capture Courtney and Matt’s wedding day. These two share a love that feels effortless and deeply rooted, and it was clear their guests felt the same joy witnessing their story unfold.

Wedding portraits at Fairlie Chicago
Wedding portraits at Fairlie Chicago
Wedding portraits at Fairlie Chicago
Guests dancing at live band wedding reception
Guests dancing at live band wedding reception
Food truck late night wedding snack in Chicago

It was an honor to capture Courtney and Matt’s day. These two share a love that feels effortless and genuine, and it was clear their guests felt the same joy witnessing their story unfold.

Courtney and Matt, thank you for trusting me to document this chapter of your lives — here’s to all the adventures, laughter, and bocce ball wins ahead.

Reach out here to inquire about wedding photography collections or view more real Chicago weddings on the Blog.

Vendor Team

The biggest cheers to these incredible vendors who made this wedding come together so flawlessly:

Planner: @stunningandbrilliantevents

Photographer: @winterlyn_photography

Ceremony / Reception: @fairliechicago

Videographer: @shutterandsound

Music: @beatmixchicago

Floral Designer: @studio__poppy

Hair: @thebridalcollective__

Makeup: @makeupbyamericaf

Photo Booth: @fotioco

Catering: @heartyboys

Food Truck: @cheesies_truck

A Modern Chicago Love Story

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Begin your journey toward preserving your love story with Winterlyn Photography, a premier Chicago wedding photographer. Every wedding is a deeply personal celebration, and we are honored to document each moment with an artful, intentional approach. From quiet, intimate exchanges to grand, unforgettable celebrations, we capture the true essence of your day with timeless elegance and emotional depth.

Secure your date today and allow us to create a visual legacy that reflects the beauty, authenticity, and spirit of your love — memories that will be cherished for generations to come.

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