Alejandro moved to Chicago in 2000 to learn from the masters. Since, he has performed at the Green Mill, the Chicago Jazz Festival, Andy's Jazz Club, Pete Miller's Steakhouse and the Jazz Showcase as a leader and a sideman for Taku Akiyama, Marco Polo, Marc Pompe, Juli Wood and the Deep Blue Organ Trio. He has performed with Jodie Christian, Von Freeman, Bobby Broom, Ron Blake, Kobie Watkins, Maurice Brown, Ron Perrillo, Eric Schneider, Pat Mallinger, Marquis Hill, Juli Wood, Dennis Carroll, Shara Maxwell, Marc Pompe and the Chicago Jazz Orchestra.

In 2012 he released his debut recording "Urban Intervals." The recording features piano legend Jodie Christian.

In 2018 Alejandro has released his second recording, his first with the group Flow.

​Flow is a guitar, piano led jazz group featuring Bill Carrothers with the all star rhythm section of Dennis Carroll and Zach Harmon.