A Rustic, Chic Wedding at Four Seasons Chicago in Chicago, Illinois

Annabel Jerkin and Matthew Terker both grew up in Manhattan, where they met as children at Hebrew school. Since the two were in the prime of their “awkward phases” – in other words, “way too many braces” – they didn’t think much of each other until they were reacquainted 12 years later, during a weekend trip to Fire Island. Matt saw Annabel from across the ferry parking lot, recognized her, and immediately asked how many of her bags he could carry onto the boat. They’ve been together ever since.

“Matt proposed at our apartment in the West Village,” Annabel describes. “Given that he called me three times that day to ask what time I would be home, it didn’t come as much of a shock. What did surprise me, though, was that Matt had rented out our favorite neighborhood restaurant for a party with our families and friends.”

The couple always knew they wanted a destination wedding, and loved the idea of spending a weekend with their favorite people. “We immediately began planning our wedding in Chicago, where Matt has spent every Thanksgiving with his many family members who live there,” says Annabel. “Every time a vendor asked us what sort of wedding we wanted, the answer was simple: fun. In every decision we faced, we asked ourselves what would be the most fun for our guests. That was particularly true when it came to selecting music – a DJ/band hybrid, Jason Fioto of Generation Events, who we had seen perform at our best friends’ wedding four years prior. Though we had only been dating for a few months at the time, we asked for their business card, joking that if we ever got married, we needed to hire them.”

Thanks to wedding planner Reva Nathan, Annabel and Matt’s wedding incorporated even their most unique requests. As soon as the groom stepped on the glass during the wedding ceremony and kissed the bride, a gospel choir burst through the doors singing “Love Train” by the O’Jays. “Seeing the surprise and delight on our guests’ faces is something we will never forget,” the bride adds. “People were literally dancing their way out of the room, and it totally set the tone for the rest of the evening.”

The night was filled with many other personal touches, including the bride’s bouquet, which was wrapped with a silk Hermes tie that belonged to her late father. As a nod to the groom’s love of Kettle One vodka, a “build-your-own Kettle One” bar was also set up, complete with various mixers and fixings. 

For the wedding décor, Rishi Patel of HMR Designs brought the bride’s vision of a rustic ambiance to life. Rather than losing momentum by asking guests to relocate for the after-party, the reception space was later transformed with nightclub-style booths, bottle service, and magnum champagne sparklers. A long night of dancing was then completed with late-night snacks of Burger King and Lou Malnati’s famous Chicago deep dish pizza.

“The whole weekend exceeded our wildest expectations,” says Annabel. “We were completely elated. When the party finally ended at 2:30 a.m., the dance floor was still full. We think it’s safe to say it was a fun night.”