Naomi and Jake’s love story came to life at The Wellsley on a late-summer day in Chicago, filled with laughter, color, and carefully curated details. The day began at the Sofitel, where Naomi and her wedding party enjoyed pampering and coffee with the Nicki Rouge Bridal Team. Jake and his crew had brunch at Tempo Café before returning to the hotel to suit up. Bradley Moss Photography captured every detail, from Naomi’s Arthur & Lucca gown to the vibrant florals by Flowerchild.
Naomi shared a first look with her father, followed by an emotional reveal with Jake on the Sofitel stairs.
While the couple took portraits around the city, the Five Grain team prepared The Wellsley for its debut to the wedding guests. Boka Catering and Flowerchild transformed the space with mossy greens, soft pinks, and pops of orange and yellow, while a floral-draped chuppah took center stage.
Before guests arrived, Naomi and Jake signed the ketubah with their families and friends. Jake’s longtime cantor officiated the ceremony with warmth and humor, guiding the couple and guests through a heartfelt celebration.
The ceremony was short and sweet with Jewish traditions.
Following the ceremony, guests enjoyed cocktail hour in the atrium with drinks and hors d’oeuvres from Boka, while the Five Grain team set up the reception. Naomi and Jake made their grand entrance to “Sky Full of Stars” by Coldplay and shared their first dance to “You Make My Dreams Come True.” Dinner by Boka was punctuated by heartfelt toasts, and a Lego-topped cake from Bittersweet added a personal touch.
Rendezvous Music kept the energy high, filling the dance floor from the hora to classic hits, with late-night snacks to keep everyone fueled (even the vendor team couldn’t help but bop along on the sidelines!). As the final song, “New York, New York,” played, it was clear that no one wanted the night to end.
Naomi and Jake, it was an honor to celebrate your love and bring your vision to life. Thank you for trusting Five Grain Events with your day.
