Maddie + Matt | A Timeless Wedding in the Heart of Chicago | The Dalcy | Chicago, IL

August 23, 2025

Weddings

iconic black tie wedding at the pendry the dalcy grant park in downtown chicago with amelia cole events by josh and andrea photography

One last stroll down the path seemed only fitting before they joined their friends on the bus. Ahead of them lay a short bus ride to a ceremony where they would say their vows, share a kiss, and begin an evening full of celebration. But for now, a final stroll as fiancés felt like the perfect thing to do. Even as Maddie and Matt walked through the heart of Chicago, the secret cove of trees seemed to quiet the rush around them. Matt led Maddie softly by the hand on a private path through the garden as they gazed up at the surrounding architecture. They knew that the memories they shared in this city so far were only the first few chapters of their story, and today, a new and beautiful chapter was about to begin.

A sentiment of thankfulness washed over Maddie and Matt’s friends and family as they awoke to a simply splendid summer morning. The threat of rain which had plagued the weekend was but a distant memory as Maddie and her bridesmaids began to prepare for the day ahead in one of the Pendry’s spacious suites. Before she departed for the first look with Matt, Maddie’s father surprised her with a beautiful bracelet with an even more beautiful story behind it, having been bought and saved 21 years ago to be given to Maddie specifically on her wedding day. Across town, Matt completed his final preparations at their apartment before joining his groomsmen on a leisurely walk through the neighborhood to the bus that would take him to the Pendry, and more importantly, his wife-to-be. Their First Look atop the private rooftop created a little “pocket of peace” where Maddie and Matt were able to take in the day and all of the memories and stories that had now led up to this day. Grant Park, only a few blocks away, provided Maddie with the portrait location of her dreams; a slightly secluded space that captured the timeless architecture of the Chicago from yesteryear combined with the lushest of gardens that harkened back to a certain engagement shoot last year in another quiet corner of Chicago’s neighborhoods. The ceremony was filled with the lives that Maddie and Matt had touched, and the cheers that arose from their first kiss as husband and wife could be heard across town and into the heavens. Even the storm that had held off for most of the day seemed to understand it needed to stay away for a few moments longer, allowing Maddie, Matt, and their guests a chance to arrive at the Dalcy before the rain began to fall. Cocktail hour spread across the covered rooftop, as Maddie and Matt were finally able to begin connecting with the people who had traveled near and far to have the chance to celebrate with them. Both the design team of Amelia Cole and the staff of the Dalcy had been tirelessly at work throughout the day, preparing the banquet room to a level of such splendor that it stole Maddie and Matt’s breath away as they walked inside for the first time. Soon, it was their turn to return the favor as Maddie and Matt brought the room to a roar with their iconic first dance, signaling to all that this would be an evening that would not soon be forgotten.

Maddie and Matt, we are still in awe of the beauty that was your wedding day. But even more than that is the beauty that your relationship displays to the world. Whenever we have had the opportunity to be around you, we have always felt the deep sense of the purpose and passion you both have towards the people in your lives. But after your wedding day, we can also clearly see how that care and love for others has translated to the incredible impact you have had on the lives of all around you. Just like the story and moments we now share below, you both have such a beautiful spirit to share with the world, and most importantly, with each other; and we are so excited to see how you continue to impact those around you in the stories to come.

All our best!

J + A

iconic black tie wedding at the pendry the dalcy grant park in downtown chicago with amelia cole events by josh and andrea photography All photos are property of Josh and Andrea Photography LLC.