Chicago Engagement Portraits by Derrick Diaz

A couple dressed in formal attire sharing a kiss on a balcony overlooking a city skyline with tall buildings and water during sunset.

Engagement sessions in Chicago, captured by Derrick Diaz, embody elegance and modern romance. Set against the city’s iconic architecture and sophisticated urban landscape, the imagery captures a seamless blend of timeless style and genuine connection. Every frame is intentionally composed, highlighting subtle gestures, refined movement, and the quiet confidence of a couple deeply in love. The result is a collection of engagement portraits that feel polished, elevated, and effortlessly luxurious—an enduring reflection of love within one of the world’s most iconic and dynamic cities.

ENGAGEMENT BOOKING INFO
A couple holding hands and smiling at each other on a waterfront with a city skyline in the background during sunset.

Milton Lee Olive Park: Chicago, IL

A couple in formal attire is at a wedding ceremony, with the man proposing to the woman on a red carpet. The backdrop features large illuminated letters spelling 'LOVE' and a heart-shaped floral arrangement made of roses. There are candles on the floor and rose petals scattered on the red carpet, with musicians playing guitar and singing nearby.

Surprise Engagement: Melrose Park, IL

A man kneeling on one knee proposing to a woman on a staircase outdoors, with greenery and a large architectural structure in the background.

Maggie Daley Park: Chicago, IL

A bride and groom sitting on a park bench, smiling at each other during their wedding photos. The bride is wearing a white wedding dress and holding a bouquet, while the groom is in a black suit with brown shoes. They are surrounded by trees with sunlight filtering through the branches.

Cancer Survivors’ Garden: Chicago, IL

A man proposing marriage to a woman on a wooded trail during sunset, with a blanket, flowers, and decor nearby.

Lake Katherine: Palos Heights, IL