Kailin and Winston’s spring downtown Chicago wedding may have been two years later than expected, but it turned out to be a perfect day in the city for their wedding. I first met this couple back in 2019 for their engagement session. We woke up bright and early to meet up for a chilly picnic on Promontory Point before heading over to the University of Chicago. They booked me for their wedding after that session, with plans to be married in 2020. With restrictions in place on their wedding date, the ended up tying the knot during an intimate rooftop wedding and postponed their big celebration to 2021 . . . and then to 2022.
When the day finally came for their big wedding day, they were just hoping for the best weather. It ended up being a perfect 60 degree, non-windy day in Chicago, which is no small miracle for this time of year in the midwest. I met up with Kailin and her girls at the hotel while they were finishing up getting ready. Kailin had the sweetest first look with her dad in the hotel room, but I am sworn to secrecy about the presence of tears or not during that moment. Once Kailin composed herself again, we headed down to have the first look with her and Winston where he finally got to see her in her wedding dress. They exchanged letters and gifts, hugs and kisses, tears and laughter. Then, we loaded up with the wedding party for photos at the Chicago Board of Trade building.
Kailin and Winston’s wedding party was the best! They were fun, kind, and so supportive of the happy couple. After hanging out with them shooting photos for a while, we headed with just Kailin & Winston to the Wrigley Building for a few photos of the two of them. They wanted iconic “Chicago” photos, and I’m so happy with what we got in both locations.
Their ceremony was then held at the historic Second Presbyterian Church on Michigan Avenue, followed by a reception at the nearby Row 24. Between the ceremony and reception, we popped over to Ping Tom park for a few more photos. On our walk into the park, Kailin was handed a bunch of yellow balloons by a lady walking out of the park who had just celebrated her birthday. We laughed and laughed about carrying around this bunch of yellow balloons, and what we were going to do with them. Of course, we had to get a few photos with the balloons before Kailin then gave them to a little girl on the playground.
The day ended with a sweet reception at Row 24. Kailin’s father gave a sentimental welcome speech, followed by a prayer by Winston’s father. Dinner was served by the infamous City BBQ and then the best man and maid of honor gave heartfelt, funny speeches. Dancing to Forever Like That by Ben Rector, Kailin & Winston shared the sweetest moment surrounded by their friends and family. It was a beautiful celebration two+ years in the making.
Kailin and Winston, thank you for having me photograph your day. It was pure joy to be a part of and I wish you all the best.
Planner: Shh Events
Church: Second Presbyterian Church
Venue: Row 24
Video: Luke Overstreet
Florist: Flowers for Dreams
Cake Artist: Susan Stanton, family
HMUA: Shannon Marie Bridal
Bridal Boutique: Bridal Boutique by New Name
Caterer: City BBQ
Suits: Suit Shop Official
To see more weddings like this Spring Downtown Chicago Wedding, click here.