Karlotta and Dan’s Chicago engagement session was full of laughter, love, and a little bit of adventure. From sharing ice cream at Margie’s Candy Shop to strolling past the Wrigley Building and setting sail on Lake Michigan, every part of their session reflected who they are as a couple — joyful, spontaneous, and deeply connected.

Vendor Credits

Photographer: The Cannons Photography
Sailboat Charter: Salty Dog Sailing Co.

A Sweet Beginning at Margie’s Candy Shop

Their engagement session began at Margie’s Candy Shop, one of Chicago’s most nostalgic treasures. Between the glow of vintage lights and the sound of old-fashioned milkshake blenders, Karlotta and Dan shared ice cream sundaes and a few quiet moments that felt like something out of a movie. The atmosphere was cozy and lighthearted, a perfect way to begin the evening.

Downtown Moments at the Wrigley Building

Next, they headed downtown to the Wrigley Building, a Chicago landmark that beautifully combines architecture and romance. The marble detailing and evening light reflected off the river as they walked hand in hand, taking in the city’s hum and charm. The skyline created a timeless backdrop for portraits that captured both elegance and ease.

Sailing into the Wind on Lake Michigan

The highlight of the evening came as the sun began to dip behind the skyline. Karlotta and Dan boarded their sailboat with Salty Dog Sailing Co. for a sunset session on Lake Michigan. What started as a calm sail quickly turned into an adventure as waves reached three to five feet high.

Even with the wind whipping through their hair and the boat rocking beneath them, Karlotta and Dan were completely at ease. They laughed, held tightly to one another, and embraced the unpredictability of the lake. The motion of the water created an energy that made every frame come alive. Their connection was undeniable, and their joy turned what could have been a challenge into something unforgettable.

We adjusted positions, steadied cameras, and made it happen for them — capturing moments that felt both cinematic and real. Those images on the water, framed by the curve of the sails and the silver horizon, became the heart of their session.

Photography Approach

For Karlotta and Dan’s engagement, our focus was on storytelling through motion. Chicago offers such an incredible mix of texture — from the nostalgic charm of Margie’s to the classic lines of the Wrigley Building and the natural expanse of Lake Michigan. We approached each location with intentional variety, blending editorial composition with genuine emotion.

The sailboat portion required adaptability, balancing the camera against the sway of the waves while preserving the soft, romantic feel of the evening. What resulted were portraits filled with movement, laughter, and authenticity.

Favorite Moments

• The playful smiles at Margie’s Candy Shop surrounded by vintage decor
• The golden light along the Chicago River near the Wrigley Building
• Karlotta’s laughter as the first big wave rocked the sailboat
• The calm that followed as the sun set over the skyline
• The way they leaned into each other, completely unfazed by the wind and waves
• The final portraits as the sails caught the evening light, perfectly still against a moving lake

Tips for Planning a Chicago Engagement Session

• Mix architecture and nature: Chicago offers both timeless cityscapes and open lake views that create a full visual story.
• Check lake conditions: If you plan to sail, watch for wind forecasts and prepare for unpredictable waves. The motion can add energy to your images.
• Keep flexibility: Some of the most memorable images happen when couples lean into the unexpected.

Ready to Begin Your Own Chicago Engagement Session?

We would love to capture your story with the same care and creativity.
Explore our Engagements or Contact Us to begin planning your Chicago engagement session — whether on land, by the lake, or out on the water.