Wilson, who gained fame from documenting his female to male transition for his now 437,000 Instagram followers, has embraced the vocal changes that came with said transitions to create a unique musical style.

The 23-year old was initially inspired by his talented mother, Cheryl Wilson. He started playing piano at the age of four and picked up the flute in middle school. At 16, he began playing guitar, singing, and songwriting.

In addition to singing, the photogenic Wilson has also done modeling work. He has appeared on the cover of Candy magazine and in underwear ads for 2(x)ist.

Jaimie Wilson performs the North Stage at 5:30 p.m. on Saturday, June 22. The annual Chicago Pride Fest takes place on June 22-23, one weekend before the annual Chicago Pride Parade. It runs from 11 a.m. to 10 p.m. down North Halsted Street from Addison to Grace. A $10 suggested donation is requested at the entrance.

This year’s festival honors the birth of the pride movement by recognizing the 50th anniversary of Stonewall.

The 2019 Chicago Pride Parade, celebrating its 50th year, is Sunday, June 30 starting at noon.

Chicago Pride Fest is organized by and benefits the Northalsted Business Alliance, the organization behind Northalsted Market Days, Frost Fest and the Halloween Parade. 

Full entertainment lineup | Chicago Pride Calendar



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