Harold Washington Library Chicago Wedding - Kayla & Phillip

Apr 7

South Rose Garden | portrait of groom dipping bride | Chicago IL

Fall Wedding at the Harold Washington Library

I’m still smiling thinking back to Kayla and Phillip’s wedding day this past fall. These two are such a fun, easy-going couple, and their wedding was the perfect reflection of their personalities—boisterous, heartfelt, and full of surprises. I’ve photographed plenty of weddings at the Harold Washington Library over the years, but this one stands out for so many reasons. It was one of those days that made me grateful all over again for what I get to do.

Getting Ready at Meaningful Locations

The day started with Kayla getting ready at her childhood home on the northwest side of Chicago. I love when couples choose places that have personal significance, and you could feel all the warmth and history of family in that space. Meanwhile, Phillip got ready at the historic Union League Club, a spot near the venue.

Ceremony at Holy Name Cathedral

Kayla and Phillip kept things traditional, so the first time they saw each other was as Kayla walked down the aisle at Holy Name Cathedral. It’s hard to describe how special this moment was, not just because of the grandeur of the cathedral but because Phillip’s father officiated the ceremony. His words were deeply personal (and hilarious), making the whole experience even more meaningful for everyone there.

Portraits at Buckingham Fountain & South Rose Garden

After the ceremony, we made a stop at Buckingham Fountain and the South Rose Garden for wedding party portraits before heading to the reception. The weather was absolutely perfect—one of those ideal fall days in Chicago with soft, golden light. It was the kind of light photographers dream about. One of my favorite images from the day is of Kayla and Phillip in the rose garden, with Buckingham Fountain framed perfectly in the distance. Although this is a popular spot for tourists, you don’t see many wedding portraits there.

A Reception Full of Shenanigans

After the ceremony, we made our way to the Winter Garden at the Harold Washington Library. This space is one of my favorite Chicago wedding venues—soaring ceilings, a glass atrium that lets in beautiful light, and the live trees and string lights give it a surprisingly intimate feel despite its size.

Phillip had mentioned early on that he loves a good “shenanigan,” and he definitely delivered. One of my favorite moments of the day was when he surprised Kayla with a book he wrote about their relationship. We took a quiet moment away from the reception to photograph them in the library stacks, and it was there that she found the book. I’ve seen a lot of wedding surprises, but this one was truly a first.

The personal touches didn’t stop there. Phillip built both the bar and the photo booth backdrop himself. The bar was crafted from reclaimed wood, with their names burned into the front. The photo booth backdrop was made from old book pages—a perfect nod to their shared love of reading.

Memorable Moments on the Dance Floor

The speeches were hilarious and heartfelt, setting the tone for an unforgettable dance party. Another surprise? Phillip brought out a baseball glove during the mother-son dance, and they played catch right there on the dance floor—a nod to the games of catch they shared when he was a kid. It was such a genuine, joyful moment that had everyone smiling (and reaching for their cameras).

Kayla and Phillip’s wedding was the kind of day that reminds me why I love photographing weddings—genuine people, real moments, and meaningful details in iconic Chicago spaces. Big thanks to Stephanie Hickey of Shh Events for making sure everything ran smoothly. And of course, to Kayla and Phillip for letting me be part of such a fantastic day.

If you’re planning a wedding at the Harold Washington Library, I’d love to chat! It’s one of my favorite venues in Chicago to photograph, and every wedding there brings something new and exciting.