He was a resident member of Chicago's Victory Gardens Theater, where thirteen of his plays—including Flyovers, Porch, The Action Against Sol Schumann, The Value of Names, Berlin '45, With and Without, Court-Martial at Fort Devens, Class Dismissed, and Bluff have been produced.
It received a Kennedy Center-American Express production grant and was cited by the American Theater Critics Association as one of the three best plays to premiere in the 1990–91 season.
Flyovers, which premiered at Victory Gardens in 1998, is a more personal project, and tells the story of a film critic who returns to the small town in Ohio where he grew up and encounters threats he thought he left behind years ago.
The original production, directed by Dennis Zacek, starred William Petersen, Amy Morton, Marc Vann and Linda Reiter.
A showcase production in New York in 2009, produced by Artistic New Directions, 78th Street Theatre Lab and Jeff Landsmann, starred Richard Kind, Michele Pawk, Kevin Geer and Donna Bullock.
Northwestern University Press also published an anthology containing nine of his scripts in under the title The Value of Names and Other Plays by Jeffrey Sweet, with a foreword by Chicago Tribune theatre critic emeritus Richard Christiansen.
His work for the soap opera One Life to Live resulted in a Writers Guild of America Award for writing for a daytime serial in 1992 and an Emmy nomination.