The crash took place just before 9 p.m. Wednesday night near 95th and Stony Island.
The chief was heading to a fire when the woman struck his department-issued SUV with her minivan. The SUV rolled over several times.
The chief was taken to a hospital in serious condition. A spokesperson for the fire department says he is going to be okay.
Three other vehicles were involved in the crash.
Several others were injured including two small children.