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City Winery Wedding | Kelsey & Brett | Chicago Wedding Photographer

Fall Chicago Wedding at City Winery

We stepped into Kelsey's getting ready room at the JW Marriott downtown Chicago to a room full of smiles and robes—sisters, friends, and loved ones gathered to celebrate alongside Kelsey! They popped a bottle of Veuve with a cheers to the bride, and got into their lavender dresses before helping Kelsey into hers. 

Just a few blocks away, Brett and the guys were watching the game at his condo. He looked out the same window he does every morning, but this time, as a groom. Brett’s mom helped him with the finishing touches of his attire, tying his bow tie and helping him with his golf club cufflinks before they made their way to see Kelsey!

When it was time to see his bride, Brett waited at the bottom of the grand staircase as Kelsey gracefully came down and tapped her groom on the shoulder. They hugged and smiled, ready to finally say “I do” with their friends and family watching! 

All day we got to hear stories from Kelsey and Brett’s family and friends, about their competitive spirit, active habits, love for golf, and amazing achievements in life. But what I’ll remember most about Kelsey and Brett on their wedding day was their calm presence and joyful spirits. We watch a lot of couples together on their wedding days, but rarely are they as grounded and present as Kelsey and Brett. During each moment, they were laughing with friends, up for anything, and enjoying the company surrounding them. 


Kelsey and Brett, what an honor it was to spend your best day with you. As Brett said in your thank you toast to the loved ones gathered under the string lights at City Winery, so many people have paved the way for your love, for your marriage. We can’t wait to see how yours will pave the way for those who will come after you. We wish you all the best as you start this adventure together! Love and hugs, Becky & Kaleb. 

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Becky Dean
I'm a Co-founder and Lead Photographer at Studio Ostendo.

Wedding photography is my heartbeat. For me, it holds the perfect tension between creativity and authenticity, observation and connection. In front of my camera clients transform to friends, and behind it you'll usually find me tearing up, cheering you on, or holding my breath because of the raw goodness of the moment at hand.

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Becky Dean, Boise Wedding Photographer at Pen and Lens Photography
Becky Dean
Co-Founder, Studio Ostendo

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