One of the greatest perks of being a Chicago wedding planner is the opportunity to truly get to know my couples and their families throughout the planning process. Maddy and Philip’s wedding was especially meaningful because it was wedding number two in an incredible family “three-peat” that I had the joy of planning over the course of 18 months.
Yes—three weddings for the same family in less than two years! By the end of it, the mother of the bride and I had become inseparable after two wonderful years of planning together.
Their celebration also allowed us to work in two of Chicago’s most iconic private club venues: The Racquet Club of Chicago and the historic Casino Club. These spaces are beloved in the city for their timeless architecture, elegant interiors, and classic Chicago charm—making them the perfect backdrop for a refined and understated wedding weekend.
A Classic and Understated Wedding Design
Early in the planning process, I asked Philip how he envisioned the aesthetic for their wedding. His answer?
“Plain.”
Naturally, that became an ongoing joke throughout the entire planning journey. Over time, “plain” evolved into something much more fitting: classic, understated, and timeless. Instead of elaborate décor, we focused on meaningful details that reflected Maddy and Philip’s story.
The design palette centered on ivory and soft greenery with accents of navy blue, a combination that complemented both the Racquet Club of Chicago and Casino Club interiors beautifully.
For the rehearsal dinner at the Racquet Club, one large U-shaped table for 80 guests created a warm and intimate setting that encouraged conversation and connection. At the reception, round guest tables and elegant banquet seating set the tone for a sophisticated evening.
Maddy and Philip were seated at a table in the very center of the reception space, allowing them to feel completely surrounded by the love and energy of their guests during dinner and toasts.
Floral and event design by HMR Designs brought the room together with understated greenery arrangements that paired seamlessly with textured linens and custom menu cards created for both events.
Meaningful Irish-Inspired Wedding Stationery
The wedding stationery was one of the most personal elements of the entire celebration.
Maddy and Philip both graduated from Notre Dame, and their relationship began while studying abroad together in Ireland. That same country later became even more meaningful when Philip proposed during a family trip overseas.
While we didn’t want the wedding to feel overly themed, we incorporated subtle Irish-inspired design details into the stationery suite created by Steracle Press.
A Celtic love knot motif appeared throughout the paper goods, including custom envelope liners and delicate borders on the menu cards. Their ceremony program also featured a charming illustration of the church accented with a small Celtic bead and Irish flag—thoughtful touches that honored their story without overwhelming the classic design.
A Lively Reception with Chicago Wedding Entertainment
Once dinner concluded, the celebration truly came alive.
The BPM Orchestra kept the dance floor packed all evening, bringing incredible energy to the reception and creating the kind of party atmosphere every couple hopes for on their wedding day.
Later in the evening, guests discovered a hidden speakeasy-style lounge where late-night bites were served and a piano man perched behind the bar led sing-along favorites well into the night.
The Perfect Late-Night Wedding Favor
As the evening came to a close, guests departed with a thoughtful and very on-theme farewell gift: an “Irish Breakfast Box.”
Inside were freshly baked scones, Irish tea, and local honey—perfect for a cozy morning after the celebration (and perhaps a little recovery after a night of dancing).
It was the perfect ending to a wedding weekend that balanced classic Chicago elegance, meaningful personal touches, and an unforgettable celebration.
And after planning three weddings for this incredible family, I can confidently say: this party absolutely rocked all night long.
Vendor Team
- LOLA Event Productions: Lavish LOLA Planning Package
- Photography: Olivia Leigh Weddings
- Venues: St James Chapel, Racquet Club of Chicago and Casino Club
- Glam Squad: Marissa Lauren Hair, Korena Robinson Hair, Shannon O’Brien Bridal
- Décor: HMR Designs, Frost Chicago, BBJ Linen, Halls Rental
- Entertainment: Beat Mix Music
- Stationery: Steracle Press
- Transportation: Premier Trolley and Signature Transportation
- Gown: Mark Ingram, Ultimate Bride
