Vandermark has lived in Chicago since autumn 1989. Since then, he has performed or recorded with many musicians (including Hal Russell, Paal Nilssen-Love, Hamid Drake, Fred Anderson, David Stackenäs, Paul Lytton, Joe Morris, Ab Baars, The Ex, Mikolaj Trzaska, Marcin Oles, Waclaw Zimpel, Axel Doerner, Mats Gustafsson, Bartlomiej Oles, Wolter Wierbos, Joe McPhee, Zu, Peter Brötzmann, Fredrik Ljungkvist, Paul Lovens, Lasse Marhaug, Yakuza, Kevin Drumm, and members of Superchunk). He first gained widespread attention while with the NRG Ensemble from 1992 to 1996. He was once a member of Witches and Devils and the Flying Luttenbachers and has led or co-led several groups, including DKV Trio, Free Fall, Territory Band, CINC, Sonore, the Vandermark 5, the Free Music Ensemble, School Days, the Sound in Action Trio, Steam and Powerhouse Sound.