Notable natives and former residents of Chesterton, Indiana include:
Academics
- Avery Craven, historian of nineteenth-century United States and the American Civil War
Athletes
Baseball
- Bill Collins, outfielder in Major League Baseball
- Ron Kittle, former Major League Baseball player
- Mickey Morandini, former Major League Baseball player
Basketball
- Bob Dille, retired basketball player and championship high school coach
- Mitch McGary, star player from Chesterton who went to Michigan; led the team to the NCAA men's final in 2012-2013
- Matt Nover, former professional basketball player and actor
- Zack Novak, former NCAA (University of Michigan) and professional basketball player (Landstede Basketball)
Swimming
- Blake Pieroni, Gold medalist swimmer and current Indiana University swimmer
Martial arts
- Eddie Wineland, MMA fighter with Ultimate Fighting Championship (Bantamweight)
Entertainers
- Jim Gaffigan, standup comedian and actor
- Taylor Zakhar Perez, actor