Cassidy & Conor
Fox + Ivory Photography
Elegant and Playful Spring Wedding at The Drake Oakbrook
Cassidy and Conor’s love story began one evening at Old Town Pour House in Chicago, when Conor’s friend encouraged him to go say hello to the woman who caught his eye. He offered to buy Cassidy a drink—and the rest, as they say, is history.
The bonded over their love of baseball, the Chicago White Sox, and the city where they met and fell in love.
As a Chicago wedding planner, I knew The Drake Hotel in Oakbrook would provide the perfect backdrop for their celebration—classic, elegant, and full of natural charm.
The couple was blessed with beautiful sunny weather. The Drake Oakbrook’s outdoor setting created a relaxed yet refined atmosphere, where every moment felt intimate and intentional. The outdoor grounds were perfect for their first look and pre-ceremony photos. Their ceremony took place beneath the venue’s picturesque gazebo, surrounded by lush greenery and spring sunshine. The ceremony felt intimate and full of personality, expertly officiated by Cassidy’s brother.
Cassidy’s vision was both sophisticated and fun, blending navy with vibrant hot pink—a palette that captured her lively personality while keeping the overall aesthetic elevated. Bridesmaids wore striking hot pink dresses that popped against the rich navy and white decor and lush floral arrangements bursting with color.
From the floral-lined aisle to the glowing sparkler exit, every detail told a story of celebration and connection. Guests signed a baseball base-shaped guest book—a playful nod to Conor’s career as a baseball announcer and their shared love for the game. The couple were over the moon to see their vision finally come together making for a successful room reveal!
As the sun set over The Drake, the energy of the evening only grew. From a heartfelt speeches, to a dinner buzzing with love and lively conversation, the ballroom the reception was full of joy, laughter, and a sense of togetherness that perfectly reflected who Cassidy and Conor are as a couple. The band kept guests dancing all night long and their sparkler exit was the ideal send-off—brimming with excitement for everything ahead.
Cassidy and Conor’s wedding was a beautiful reflection of their story—elegant and heartfelt, with moments of genuine fun woven throughout. From that first meeting at Old Town Pour House to the laughter that echoed across The Drake’s Three Oaks Room their day was a testament to saying yes to connection, courage, and love.
The Details:
Birdcage and Blushers: Partial Wedding Planning
Ceremony & Reception: The Drake Oakbrook
Photography: Fox + Ivory Photography
Band: Bluewater Kings Band
Florist: Avant Gardenia
Dancefloor Wrap: Prestige Wedding Decoration
Hair & Makeup: Windy City Glam
Bridal Gown: Viero Bridal
Considering tying the knot at the Drake? Contact us today to learn how we can bring your wedding to life at this luxury wedding location!
