Art Institute of Chicago Engagement

There’s something so timeless about fall in Chicago with the golden leaves, the crisp air, and the beautiful sites of the city as the seasons shift. Caroline and Alex’s Art Institute of Chicago engagement session perfectly captured that feeling. It was a classic October day in Chicago with cool temps and overcast skies. The vibe, however, was effortlessly romantic.

Timeless engagement portraits at Art Institute of Chicago

I first met Caroline when I photographed her sister Katie’s, Elegant Chicago Winter Wedding at The Drake Hotel. It’s always such an honor to be invited back to capture another milestone within the same family, and this session was no exception. Caroline and Alex are planning a fall wedding at Theater on the Lake next year, so this cozy, autumn session felt like the perfect reflection of their story and their upcoming celebration.

couple walk outside of art Institute of Chicago

engagement portraits on steps of building

We started their session at the Art Institute of Chicago, surrounded by timeless architecture that made everything feel so classic. They knew from the start that they wanted portraits in a museum setting with traditional architecture as the backdrop. Caroline looked effortlessly elegant in a chic cream top and long skirt, while Alex wore tan slacks and navy jacket. The two of them fit right into the setting of Michigan Avenue as they sat and laughed together, sharing quiet moments between portraits.

romantic engagement photos of couple sitting on stairs at Art Institute of Chicago

engaged couple walking outside of museum in Chicago

Grant Park Engagement Portraits

After exploring the museum grounds, we made our way toward Grant Park, where the city was painted with beautiful fall colors. For this part of the session, they changed into something a bit more relaxed and casual. Jeans and cozy sweaters perfectly suited the location and season. Caroline and Alex mentioned that one of their favorite things to do together is go on walks, so this part of the session felt especially natural. The two strolled through the park, hand in hand, surrounded by the warm tones of autumn, simply enjoying being together.

Engagement session at Art Institute of Chicago

Caroline and Alex’s Love Story

Their love story began in the fall of 2020, when they met on Hinge and shared their first date over drinks at The Butcher’s Tap in Lakeview before heading to Crosby’s Kitchen for dinner. A couple years later, Alex proposed to Caroline at Honeycomb during a walk around South Pond in Lincoln Park. Alex surprised Caroline by telling her they were going to meet her sister and her sister’s boyfriend for lunch across the street from South Pond so the walk was just to kill time beforehand. Little did Caroline know the walk was all part of the plan.

couple lean in together with fall trees in the background

When describing their relationship, Caroline and Alex chose the words compassionate, enduring, and adventurous, and after spending time with them, it’s easy to see why. Their connection feels steady and joyful, like two people who truly love exploring life together, side by side.

The couple wanted a beautiful fall engagement session to complement their fall wedding at Theater on the Lake, and it was an honor to capture these engagement portraits for them and document this beautiful chapter in their story! Congratulations, Alex and Caroline!