After doing college radio and journalism in Atlanta, Will Miles moved back home to Chicago in 2005 to further pursue his passion of comedy. He went through the improv training program at iO and began hitting the open mic circuit.

He has now been in the Cleveland Comedy Festival (2010), Laughing Skull Festival (2010), Snubfest (2010), won "Best of the Fest" in the Ingenuity Fest (2011), as well as winning the runner-up spot in the Break.com "Better Way" video contest (2011). He has been featured on Hannibal Buress' "My Name Is Hannibal" tour and is a regular feature at all of Chicago’s greatest clubs, where he has worked with such acts as Aries Spears, Felipe Esparza, Eric Andre, Neal Brennan, Jerrod Carmichael, and Bill Bellamy.

He also co-hosts a show in Chicago called Two Black Dudes and an Open Microphone on the last Tuesday of every month at Town Hall Pub with fellow comedian Clark Jones. He can also be heard occasionally contributing to Vocalo (89.5 FM Chicago) Radio's The Morning AMp show with Brian Babylon and Molly Adams.