Chicago Surprise Proposal | The Robey Chicago

Written and Photography by Winterlyn Photography

Ben contacted me a week ago and told me all about the SURPRISE proposal he had planned, along with his family, at The Robey Chicago. He was going to ask his lovely gf, Alex, to marry him on the rooftop of The Robey and it had to remain a surprise. My first time shooting at The Robey did not disappoint. The weather was typical for a spring day in Chicago. Overcast and rainy but we don’t ever let a thing like rain ruin a surprise proposal.

The older architecture and skyline view is everything you could want when planning such an event. Ben and Alex made their way up to the rooftop where I awaited, hiding in plain sight, and made their way to the balcony. Little did Alex know but Ben’s sister was hiding in the washroom waiting for them to arrive so she could film the moment. Ben’s immediate family had come into town and were waiting in the lobby for the signal that they could come up and congratulate the happy couple.

Alex was so excited and so full of emotion when she saw Ben reach into his pocket! I was so excited for them both and could tell this was a dream come true for both of them. Alex of course said YES! and Ben slipped on her new lifelong accessory. Her beautiful diamond engagement ring. Ben’s family came up just in time and hugged the newly engaged couple. Little did Alex know but not only had Ben’s family help with her proposal but a get-together with close friends and family was awaiting her back at their place. It was such a wonderful experience documenting this amazing new season in Ben and Alex’s life and I can’t wait to send them the full gallery. Enjoy this small sneak peek.