Love, Chicago Style: 3 Swoon-Worthy Real Chicago Weddings

weddings: Natalie Stone and Caleb Pearson

Three sets of Chicago newlyweds share the stories of their unions, adding to the patchwork of personal, beautiful, and truly unforgettable ways our city’s sweethearts say I do.

Natalie Stone and Caleb Pearson

Chicago Botanic Garden, Aug. 26, 2017

weddings: Stone Pearson bridal party

When the universe sends you a sign, you take note — and if you don’t? No worries, it’ll just send you another. Such is the case of Natalie and Caleb, who worked together in New York City, but didn’t realize they had a romantic connection until the universe stepped in and moved Caleb right across the street from his future bride.

“We kept our relationship a secret from our coworkers for an entire year, until we had to announce that we were leaving the company and moving to Chicago together,” says Natalie, a former Make It Better intern. “To this day, we have no idea how we dated — and even lived together — for so long without anyone finding out about us.”

Once the lovebirds came clean to their colleagues and moved to Chicago, Natalie’s hometown, they wasted no time making their intentions clear.

“Caleb moved to Chicago a month before me, and the night I flew in, he proposed,” she remembers.

A little over a year later, the wedding festivities began with a rehearsal dinner at the Deer Path Inn in Lake Forest. The following evening, surrounded by 175 guests, the pair tied the knot in a ceremony officiated by a mutual friend at Chicago Botanic Garden.

“We fell in love with the venue because we will be able to revisit it and have that memory for the rest of our lives, which isn’t possible at a lot of other places,” says Natalie.

weddings: Stone and Pearson

Cocktails, dinner, and dancing soon followed, punctuated by memorable speeches and late-night ice cream cones. The highlight of the night? A photo booth, which the couple ordered on a whim at the very last moment (surely, another sign from the universe).

“We weren’t planning on having one, but looking through all the pictures on the day after the wedding ended up being one of our favorite moments,” says Natalie. “It was so surreal to see people who didn’t previously know each other having so much fun together.”

Melissa Parker and Caitlin Robinson

Peggy Notebaert Nature Museum, June 18, 2016

weddings: Melissa Parker and Caitlin Robinson

If surprises are the spice of life, then Melissa and Caitlin are doing something right. Hitting it off — and knowing they had something special — within minutes of meeting was the first unexpected delight of their relationship. A year later, along came the second surprise.

“Caitlin asked me to marry her on a Friday night along the Chicago riverwalk,” says Melissa. “The next morning, I asked her to marry me by blindfolding her and taking her to her favorite place in the whole world, Wrigley Field.”

Number three showed up in the form of their wedding venue.

“We visited a number of locations with our planner, Heather, before deciding on the Nature Museum,” says Melissa. “She’d suggested it right away and we said no, but she was right!”

weddings: Parker and Robinson

With a location booked, the couple wasted no time planning the rest of their details, including a rehearsal dinner at Dinosaur BBQ in Lincoln Park. And then, a year after getting engaged, Caitlin and Melissa exchanged self-penned vows in a beautiful outdoor ceremony in front of 225 of their friends and family. Cocktails, dinner, and dancing soon followed, and then it was time for surprise number four, this time to the delight of their guests: a choreographed dance to the song “Now That We Found Love” by Heavy D & the Boyz.

“The looks on everyone’s faces as we danced said it all — no one would have ever guessed that Caitlin would do that,” says Melissa.

weddings: Melissa Parker and Caitlin Robinson (cake)

Number five was the wedding cake, a gluten-free confection with a rainbow pattern hidden inside. Number six? The accompanying ice cream sundaes, served ballpark-style in little Cubs hats, a curveball from Melissa to Caitlin. And finally, to round out the evening, lucky number seven: “A recap video of the day produced by the videographers on site and shown to guests at the end of the reception,” says Melissa.

As for surprise number eight? We’ll let you know when we do!

Young Moon and Matthew Saretsky

Chicago Cultural Center, Oct. 29, 2016

weddings: Young Moon and Matthew Saretsky (Chicago skyline)

If you’ve ever needed proof that opposites attract, here it is: When Young and Matthew first met, in a 65-student section during their first year at Northwestern Pritzker School of Law, “Young was an ostensibly serious student, sitting in the front row of each class and furiously typing notes on her laptop, whereas I sat quietly in the back of the class with a pen and pad of paper,” says Matthew. And yet, three-and-a-half years later, during a weekend trip to Sedona, Matthew found himself down on one knee asking Young to marry him. After a heartfelt YES, the Midwest natives agreed that a fall wedding in an iconic Windy City location best reflected their vision and aesthetic, and plans for a celebration at the Chicago Cultural Center were soon underway.

weddings: Young Moon and Matthew Saretsky

Thirteen months later, on a Friday night in late October, guests from near and far came together for a rehearsal dinner at Café Ba-Ba-Reeba! in Lincoln Park. The next day, with 265 of their loved ones looking on, Young walked down the aisle to her favorite piece by Debussy, and the couple sealed the deal in a ceremony that blended both Catholic and Jewish traditions.

“We also lit a candle in memory of my mother, who passed away just three months before the wedding,” says Young.

weddings: Young Moon and Matthew Saretsky (paebek)

Guests were treated to a paebek, or ancient Korean wedding ceremony, during cocktail hour, and then it was time for dinner and dancing to everything from Motown to Top 40 hits.

“My favorite part of the night was seeing so many friends and family from different geographies and time periods in our lives,” says Matthew. “It was so humbling to know that everyone made the effort to celebrate with us.”

As the night wound down, guests were treated to Chicago-style hot dogs and Detroit Coney dogs, late-night snacks as opposite — and yet perfectly complementary — as the happy couple themselves.




Cara Sullivan is Make It Better’s Executive Editor. She has held positions at Cosmopolitan, Allure, and Martha Stewart Weddings magazines, and writes for many national and local publications. Sullivan lives in Ravenswood Gardens with her husband and two young daughters, and is a passionate supporter of Indivisible Chicago, a grassroots organization that focuses on direct actions that small, local groups can take to influence their representatives in Washington. 


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