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Sasha Colby’s relationship with Chicago is deeply rooted. The drag superstar reminisced about her time living in the Windy City from 2006 to 2012, describing it as a period filled with memorable experiences on Halsted Street and at local venues like the Baton. Her many visits to Chicago, including a recent appearance at Thalia Hall, have cultivated a special bond with the city’s arts scene and its passionate drag community.
When asked about her favorite traditional Chicago foods, Sasha immediately mentioned the iconic Chicago Dog from Portillo’s, emphasizing her love for the local cuisine. Her enthusiasm for the city's summer festivals, especially Market Days, and her affection for lazy days lounging at Lake Michigan, paint her as a true Chicagoan at heart.