Engagement Photos in Chicago | Heather & Tony

Engagement photos with a city vibe on Chicago’s historic downtown streets

When Heather reached out to us about destination engagement photos in Chicago, we knew it would be the perfect place to bring her vision to life. Heather and Tony love visiting Chicago together from their home in California, especially since it brings back so many memories from when Tony lived there. Chatting about the vision they had for their engagement photos, Heather told us how much they love the architecture and charm of Chicago. It’s special in the way its history feels rich and the place feels grand, but you’re still able to find your place there on an intimate scale. 

Engagement photos that capture Chicago’s charm and the adventure of exploring Chicago

We all flew in for Heather and Tony’s engagement photos in Chicago, and they made the most of their trip:  visiting museums, having drinks at Cindy’s Rooftop, even going to the Bears game after their session with us. 

We met at the London House before walking around some of Chicago’s iconic locations together. We strolled along the Chicago riverwalk, stopped at the Wrigley Building, walked across some of Chicago’s characteristic red bridges, and ended our time together taking in the sweeping skyline views at North Avenue Beach. 

couple looking at one another
street light globes in Chicago
couple walking at North Avenue beach in front of Chicago's skylinek
couple downtown Chicago
white dress with bow and black suit
couple twirling in front of Chicago skyline

Tying the style of their engagement photos to the design of their wedding

Heather and Tony are planning a Palm Springs wedding next year with an old Hollywood feel, and wanted their engagement photos to share notes of that design. When it came to fashion for their session, Heather stuck to neutral colors, but incorporated a signature piece—her white fitted dress featuring a bow at the waistline. Paired with Tony’s classic black suit, their attire echoed the effortless but signature style of old Hollywood icons. Against Chicago’s rich architecture including its neoclassical copper sconced globe lights, ornate gold doors, and striking skyline, Heather and Tony fit right in. 

couple hugging next to the Chicago riverwalk
couple walking in Chicago
couple kissing in front of gold door at the Wrigley Building
white dress with bow

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Casual conversation during their engagement photos in Chicago

As we walked through the city together, stopping to take engagement photos along the way, Heather and Tony told us all about how they met. We talked about how sweet it is to be friends first before jumping into a romantic relationship. We could tell as we photographed Heather and Tony that they really have the best time together, that their friendship is the foundation of their relationship. We love how their engagement photos echo the feeling of a date night in Chicago, while also revealing moments of connection between the two of them.

couple walking at North Avenue Beach
couple looking at each other at the Wrigley Building
couple holding hands

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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

Ostendo.Photography Blog

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