Chic Chicago Yacht Wedding & Tortoise Supper Club Cocktail Hour

A yacht wedding in Chicago was the perfect way for Brendan and Alexa to celebrate a day that blended tradition with personality. I went to college with Brendan and photographed his sister’s wedding back in 2022, so I was excited when he reached out!

From meaningful locations to thoughtful details, I loved how Brendan and Alexa mixed classic moments with non-traditional touches throughout their day, and it was all set against some of their favorite Chicago backdrops. It was also such a pleasure working alongside Kait of Celebrait by Kait, whose thoughtful planning helped everything flow seamlessly!

The Details, Getting Ready, & First Looks

The day started at a hotel overlooking the Chicago River. Alexa got ready alongside her bridesmaids while my second shooter spent time with Brendan and his groomsmen. Alexa and Brendan chose not to have a first look together. Instead, Alexa shared emotional first looks with her bridesmaids and her dad, which were some of the sweetest moments to capture!

She wore a simple, sleek high-neck gown with an open back that felt timeless and elegant, and she looked absolutely stunning in it! It was the perfect dress for a Chicago wedding day that balanced classic tradition with personality.

A Saint Clement Catholic Church Chicago Wedding Ceremony

Brendan and Alexa’s Catholic ceremony was held at Saint Clement Parish in Chicago. This church is stunning in both its architecture and atmosphere! All Catholic churches are beautiful, but this one felt especially meaningful. It had beautiful ornate details, soaring ceilings, and soft lighting that filled the space.

Their priest delivered a heartfelt homily that had guests both laughing and wiping away tears. It was a true reflection of the joy and depth of the moment. As a Catholic myself, I understand how sacred these ceremonies are. It was an honor to document such an important part of Brendan and Alexa’s wedding day. A few of my favorite images are the moments captured from the choir loft by my second shooter!

Lincoln Park South Pond Wedding Photos: The Wedding Party & Newlyweds

After the ceremony and family photos, we hopped on a trolley with the wedding party for portraits around Chicago. Our first stop was The Wiener’s Circle, an iconic hot dog stand Brendan and Alexa frequent, where the owners even personalized the sign for their wedding day! Brendan and Alexa know them, so it didn’t take much convincing.

From there, we headed to Lincoln Park’s South Pond, a meaningful spot where Brendan and Alexa take their daily walks. The classic black-and-white attire paired beautifully with the greenery and skyline, creating those timeless Chicago wedding photos. It was the perfect transition before the celebration continued with their yacht reception later that evening.

Tortoise Supper Club Wedding Cocktail Party in Chicago

Brendan and Alexa chose to shake things up by splitting their reception into two parts. They started with an intimate Tortoise Supper Club cocktail party in Chicago. They rented out the space where they had their first date, which made it such a special setting for cocktail hour, dinner, speeches, and dances. This part of the day was filled with great cocktails, the best appetizers, and ’80s and ’90s music. The warm lighting, leather booths, and classic supper club atmosphere created an inviting space for guests to relax and celebrate together.

This was such a thoughtful and personal touch that really set the tone perfectly before their night continued with their Chicago yacht wedding after-party. It really made the transition from supper club to party feel seamless and intentional!

The Kitzes’ Chicago Yacht Wedding After-Party on the Anita Dee II

To wrap up the night, Brendan and Alexa hosted an unforgettable Chicago yacht wedding after-party aboard the Anita Dee II with Anita Dee Yacht Charters. After heading to the marina, we took a few evening portraits along the docks, with sailboats lining the water and the city just starting to glow. It was the perfect transition into the party that followed!

Once guests boarded the yacht, the party kicked off immediately. Drinks were flowing, the dance floor stayed packed, and the energy never dipped. Their guests absolutely SHOWED UP! From glow sticks, singing, dancing, and laughter echoing across the deck, this Chicago yacht wedding reception felt fun, carefree, and so true to Brendan and Alexa. It was one of those nights you wish you could relive, and I’ll never forget celebrating alongside them as they closed out their wedding day on the water! Cheers to the Kitzes!

Thinking About a Multi-Location or Chicago Yacht Wedding?

One of the things I loved most about Brendan and Alexa’s day was how they didn’t limit themselves to one venue or one vision. Every part of the day felt thoughtful and intentional! From their ceremony to a Tortoise Supper Club cocktail party, and finally an unforgettable Chicago yacht wedding after-party.

Each stop really reflected who they are. They chose locations that truly mattered to them and moved through the city with ease. You could feel how meaningful the day was because they designed it that way, right down to the smallest details.

If you’re looking to treat your guests to something truly memorable, a reception with Anita Dee Yacht Charters is absolutely worth considering. If you’re searching for a Chicago wedding photographer who documents days like this with a natural, timeless approach, I might be the perfect fit! You can learn more about me here, and if I sound like the photographer for you, I’d love for you to inquire with me here. Be sure to check out the blog for more wedding inspiration and ideas!

Kind Words from the Wedding Planner:

“Riley is phenomenal! She communicates well and is so kind and flexible. As a Wedding Planner I definitely recommend her.” – Celebrait by Kait

Riley Trott Photography | Chicago Wedding Photographer

Vendors:

Photographer: Riley Trott Photography
Wedding Planner: Celebrait by Kait
Ceremony: Saint Clement Catholic Church
Cocktail Hour: Tortoise Supper Club
Yacht: Anita Dee Yacht Charters (Boat: Anita Dee II)
DJ: Standing Ovation DJ’s
Florist: Flowers for Dreams
Hair: HMB Hair
Makeup: Alyssa Lynn Makeup