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  • Writer's pictureCharlie and Taylor

Capturing Love in the Heart of Chicago: Olivia and Jack’s Engagement Session


Chicago, with its stunning skyline, vibrant culture, and picturesque landmarks, served as the perfect backdrop for Olivia and Jack’s engagement session. This memorable day was meticulously planned, starting exactly one year before their wedding, capturing their love story in the most elegant and heartfelt way.


Couple kissing during Mexico Destination Wedding ceremony

A Riverwalk Romance

We began the session at the iconic Chicago Riverwalk. The sun was shining, reflecting off the river’s surface and creating a magical atmosphere. Olivia and Jack, dressed to impress in chic outfits, effortlessly blended into the sophisticated urban landscape. Olivia wore a stylish dress that complemented Jack’s sharp suit, embodying the essence of modern romance.


As we strolled along the Riverwalk, Olivia and Jack's chemistry was undeniable. Their shared smiles and laughter painted a picture of genuine happiness.

From High School Sweethearts to Lifelong Partners

Olivia and Jack’s love story began in high school. Over the past seven years, their bond has only grown stronger, leading to a heartwarming proposal at the Garfield Park Conservatory. Jack’s proposal was nothing short of perfect – a sweet and sentimental moment that Olivia will cherish forever. He even planned two surprise engagement parties, bringing together friends and family to celebrate their love.



Portrait of bride

A Toast to Love at Ciccio Mio

After our scenic Riverwalk shoot, we headed to Ciccio Mio, a cozy bar known for its charming ambiance. Here, Olivia and Jack could relax, share a toast, and enjoy each other’s company in a more personal space.


The warm, inviting interiors of Ciccio Mio, with its vintage decor and soft lighting, added a romantic touch to the photos. Olivia and Jack’s chic outfits looked even more glamorous against the bar’s stylish backdrop. Their effortless elegance and the bar’s unique charm created a series of stunning photographs that beautifully encapsulated their love story.


Detail photo of tropical wedding bouquet at Mexico Wedding



The Magic of Their Story

Every engagement session is special, but Olivia and Jack’s was truly magical. From the scenic beauty of downtown Chicago to the intimate charm of Ciccio Mio, every location highlighted their deep connection and love for each other. Their journey from high school sweethearts to planning a wedding is a testament to their enduring bond and commitment.


As we look forward to capturing their wedding day, this engagement session stands as a beautiful reminder of their love and the exciting journey ahead. Congratulations, Olivia and Jack – here’s to a lifetime of happiness!



If you are you looking to hire the Best Chicago Destination Wedding Photographer to capture the essence of your wedding day in Chicago, you can find us here. We would love to help you craft and document your most magical day in Downtown Chicago.

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