Downtown Chicago Engagement Photos

You never really know where you’ll meet your person—sometimes it’s a random Tuesday, and sometimes it’s a five-week Skeeball league in Chicago. That’s how Jess and Ben’s story kicked off, and three years later, they’re planning a wedding at Cafe Brauer and taking downtown Chicago engagement photos to celebrate the city they’ve grown to love and call home.

Navigating Downtown Chicago for Classy Engagement Photos

Downtown Chicago was doing the most the night of Jess and Ben’s engagement session. It was one of those classic May evenings—technically spring, but definitely cold enough to question your outfit choices. The streets were packed, the wind had an agenda, and half the popular photo spots had a line.

Instead of getting stressed, Jess and Ben leaned into it. We dodged tourists, laughed at the chaos, and people-watched while we waited for spaces to clear. There’s something special about documenting love in the middle of a city that never slows down. It forces you to pause and find quiet moments in the noise. They stayed connected and fully present, even with all the commotion.

The Sweet Spot Between Candid & Confident

Jess and Ben told me from the start—they wanted their photos to feel mostly candid, laid-back, and not too forced. But also, no one wants to look awkward in front of the camera. So we struck that perfect balance: natural moments, with just enough guidance to help them feel confident and look good doing it. I’m all about reading the vibe—knowing when to give direction and when to step back and just let things unfold. With Jess and Ben, it was easy. I mostly just helped them settle into the moment. Their session came to life in all the right places. The city gave us texture, movement, and light that felt just right.

Check out Emily and Eamonn’s engagement session in downtown Minneapolis.

Chicago Engagement Photographer

If you’re dreaming up your own Chicago engagement session, let this be your sign to make it happen. These kinds of shoots are a chance to get comfy in front of the camera, shake off the nerves, and make space for real connection before the big day.

I have more Chicago sessions on my calendar next year, and I’m so excited! If you’re planning a wedding here—or just want engagement photos in an iconic city—I’d love to hear from you.

You in? Book here!