The victims say that up to six men walked up to them, pulled out guns and stole their belongings.
In one incident, the robbers ran off. In another incident, they hopped into a silver Hyundai with temporary tags and took off.
One robbery happened on the afternoon of April 14 on South Bishop Street. The other happened the next day around noon on South Elizabeth Street.
If you have information, call Chicago Police at 312-747-8380.
Sun-Times Media Wire contributed to this report.