Thirty-one-year-old Datqunn Sawyer and 51-year-old Kevin Sharp are in custody.
Sawyer faces several charges, including sexual trafficking of minors and sexual trafficking by force.
Sharp is charged with federal pandering.
A third man, 30-year-old Waymond Orr, is also charged with federal pandering. He remains at large.
Sawyer is accused of operating the child prostitution ring in his home and in his mother's home. Both are on Chicago's West Side.
Prosecutors say Sharp and Orr worked as Sawyer's drivers and enforcers.
