Alex + Taylor: Chicago Proposal at The Rookery

Alex reached out to me in the winter with plans to propose to his girlfriend, Taylor. He had a clear and creative vision — something different from the traditional proposals often seen at The Rookery in downtown Chicago. Instead of using the iconic staircase for the moment itself, Alex and his family thoughtfully designed a more personal vignette within the space, creating an intimate and emotional setting for their proposal.

Taylor wasn’t completely surprised when she arrived — her best friend had whisked her away earlier that day for a manicure and dress shopping at Nordstrom. By the time they were browsing dresses, she had a feeling something big was about to happen.

Despite the rainy, gray skies outside, the proposal glowed with warmth. The Rookery, a historic architectural gem in Chicago’s financial district, was the perfect backdrop. With its stunning Art Deco details, spiral iron staircase, and iconic glass ceiling, it offered a cinematic, timeless feel that paired beautifully with the couple’s joyful energy.

As a documentary-style Chicago engagement photographer, it was an honor to capture this heartfelt moment on both digital and 35mm film. Their love lit up the room.

Planning a proposal or engagement session in Chicago? Whether it’s a surprise proposal at The Rookery or a laid-back evening in your favorite neighborhood, I’d love to help you document it in an intentional, honest way.

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