Police said a vehicle was stolen at gunpoint by three men in the 400-block of West Wisconsin Street on the city's Near North Side just after 5:05 a.m.
The stolen vehicle was later involved in a three-car at Cornell Drive and Hayes Drive, police said.
Two men, 26 and 59 years old, were taken in serious-to-critical condition to University of Chicago Medical Center, according to the Chicago Fire Department. One of them was driving the stolen vehicle, police said.
One person is in custody and police said a weapon was recovered from the scene.
Area Central detectives are conducting an investigation.
The Sun-Times Media Wire contributed to this report.