Cavallari posted a photo on Instagram Monday, explaining why the city will "always be a special place for us."
"Not only we're [sic] all 3 of my babies born here, it's where it all began with jay," she wrote.
Cavallari grew up just outside Chicago in suburban Barrington, Ill., and moved to Chicago after she and Cutler were married in 2013.
The reality TV star said she enjoyed reconnecting with her mother and old friends, writing "a lot of people don't know I lived here when I was younger."
But two years ago, Cavallari said in an interview with Elle that Chicago doesn't feel like home to them.
"Jay hates LA," Cavallari told ELLE.com in 2015. "And Chicago's just not home."
At the time, she said she hoped the couple would live full-time in Nashville when his contract with the Bears is up.
It's unclear where the couple will relocate. Cutler has not yet announced his next move since he was released from the Bears earlier this month.