All About Kristin Cavallari's Love-Hate Relationship with Chicago, from It's 'Just Not Home' to 'I'm Really Gonna Miss This Place'

Photo: Kristin Cavallari

Chicago might be a “special place” for Kristin Cavallari now, but she wasn’t always so attached to her Midwest home base.

Cavallari announced in an Instagram post on Monday that she and her family — husband Jay Cutler, 33, and their children Camden, 4, Jaxon, 2, and Saylor, 4 months — are planning to leave the Windy City for good following Cutler’s transition from Chicago Bears quarterback to free agent. In the post she writes, “I’m really gonna miss this place,” but the Hills alum, 30, didn’t always feel so warm and fuzzy about her home in Illinois.

The reality star and designer settled in Chicago after marrying Cutler in 2013. But two years later she still wasn’t convinced it was right for her family. She told Elle in 2015 that the couple planned to make Nashville their forever home after Cutler’s contract expired.

“Jay hates L.A.,” she said. “And Chicago’s just not home.”

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She also wasn’t shy about the toll she imagined it would take on her career. According to The Chicago Tribune, Cavallari called living in Chicago a career “sacrifice” in her book Balancing In Heels, though she adds it’s “one I’m OK with for now.”

In the Elle feature, she alluded to her icy attitude toward the city stemming from the distance it would put between her and the entertainment industry she has relied on since her days on MTV’s Laguna Beach.

“I was a little nervous at first, to be honest, just because I didn’t…it’s sort of always been ingrained in me that if you want to be in the entertainment business, you either have to be in L.A. or New York,” she said. “And so when I married Jay, I officially moved to Chicago. I was a little scared.”

Chicagoist theorized in 2016 that her hesitance to embrace the city originated with an unpleasant encounter with the police force in the suburb of Evanston three years earlier. In September 2013, Cavallari was pulled over for speeding and subsequently required to pay a fee for driving with an out-of-state license for more than 90 days after becoming a permanent resident, according to the Tribune. “Who knew having a California drivers license in Illinois was a CRIME to be escorted to the police station to post bail?!!” she tweeted of the incident.

Over her almost four years of marriage to Cutler and the birth of her second and third child, Cavallari’s feelings about Chicago seem to have thawed. The lifestyle guru often shared photos of the young family cooking and relaxing in their kitchen, and supporting their favorite football team — all memories she won’t soon forget.

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“Not only were all 3 of my babies born here, it’s where it all began with Jay, it brought me closer to my mom who has become my best friend, I’ve made some amazing girlfriends, and I’ve really enjoyed being back here (a lot of people don’t know I lived here when I was younger),” she continues in her Instagram tribute. “Thanks for all the good times, Chicago.”

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