Christopher Esbrook orchestrated the proposal to his beloved, Tracy Clifford, down to the last detail. While on a trip to Cabo San Lucas, he rented the top floor of the resort where they were staying for a private dinner overlooking the ocean. Christopher asked for Tracy’s hand in marriage over a glass of Champagne with an engagement ring featuring a brilliant, classic round diamond. Afterwards, the couple retreated to their villa, where the room had been covered in rose petals and a warm bath awaited Tracy.

What Christopher didn’t count on was Tracy figuring out the evening’s occasion. The telltale sign was his shaving kit in the safe. Tracy thought this odd and investigated – only to find the ring box tucked inside the bag. Although she peeked into the safe nine times throughout the day, Tracy didn’t dare take a gander at the ring because she wanted to be surprised. Tracy maintains, “It was my dream proposal.”

Planning the wedding was a family affair with Christopher taking charge of the food, Tracy’s father selecting the wine, and her mother coordinating everything else. “She is a phenomenal host and event planner,” explains Tracy. “She helped me with everything down to the last detail. We had an amazing time!”

On the day of their wedding, Tracy and Christopher shared their most memorable moment before saying “I do.” Wanting to be present to greet guests during the cocktail hour, the couple scheduled their photo session before the ceremony. “It was important to have a few moments alone and make the first time we saw each other a special memory,” explains Tracy. “It was one of the few times that we had to enjoy each other in private that was just about the two of us.”

Raised Catholic, it was important for the couple to have a traditional mass. Upon walking through the doors of Old Saint Patrick’s Church – one of Chicago’s first churches – from the snowy evening, guests were welcomed by the interior’s warmth. Seasonal red and vanilla poinsettias, along with ivory candles, perfectly complemented the awe-inspiring architecture. Three clergymen, including a priest and deacon who are dear family friends, officiated the ceremony.

The radiant bride made her grand entrance in a white strapless gown with a thin gold band around the waist and a bustle train beautifully accented by two wide swaths of soft bullion and silver hues. Her elegant updo was adorned with a hair comb custom made from the Chantilly lace of her mother’s wedding gown and embellished with pearls and rhinestones. A pearl necklace, bracelet, and earrings added a classic touch. Tracy carried a nosegay of white peonies and ranunculuses, with the petals of a center flower flecked with fuchsia lending a bit of color, wrapped in the same fabric as her gown. The groom looked dapper at the altar in a midnight blue tuxedo.

Not wanting a conventional reception venue, Tracy had her heart set on the Modern Wing of the Art Institute of Chicago. “I love art and was enticed by the endless possibilities for décor,” she says. A fashion consultant who has worked with leading designers, Tracy’s expertise certainly influenced all the stylish details. She was inspired to recreate the “romance and lightness that comes with the idea of falling snow,” while bringing warmth to the modern space. Icy blue uplighting and projected snow flurries illuminated the 30-foot ceiling, soaring skylights, and walls, as pin spot lighting bathed tables in amber tones. A palette of soft white, cream, gold, and green combined to invoke a cozy dining experience.

Round tables swathed in golden tablecloths emblazoned with a diamond and fleur-de-lis pattern were bedecked with three dramatic centerpieces that drew the eye to appreciate various levels of the space. The central design was a six-foot-tall gilded trumpet vase bursting with a bevy of snowy calla lilies – the flower favored by Tracy’s mother – and Hawaiian orchids, surrounded by crystal candlesticks with rock crystal votives. The second featured urns overflowing with white amaryllis and Hawaiian orchids sitting atop Art Deco–inspired risers with a suspended slice of malachite. The third was composed of an illuminated rock crystal bowl filled with ivory peonies offset by Art Deco-style gold and Lucite candlesticks holding cream pillar candles. To commemorate Tracy’s grandmother, who had recently passed away, each place setting was adorned with a gardenia – her favorite flower.

From the cocktail hour to the elegant sit-down dinner, planning the perfect menu with Tony Mantuano of Spiaggia was a resound success. “The appetizers that Tony prepared for our cocktail hour were unlike anything at any other wedding that I have been to,” affirms Christopher. “We had stations of Italian delicacies including prosciutto de Parma, a wheel of parmesan, assorted seafood, and a selection of flatbreads. The guests loved the variety.” After whetting their appetites, guests enjoyed four courses followed by a sweets table. Drinks were dispensed from ornate bars custom built of illuminated malachite panels covered with an intricate gold geometric pattern and finished with dark green leather countertops.

Made by the groom’s cousin, who specializes in wedding cakes, the white four-layer confection was embellished with emerald-hued jewels and featured a cannoli filling. Guests were given pieces in specially made boxes to take home. But the festivities were far from over – they just moved to another venue for the circus-themed after-party and continued into the wee hours of the morning. “The whole night was perfection,” says the bride.