The victim arranged a sale with the 16-year-old suspect using an app, was then carjacked and forced to use his credit card at multiple locations.
Police are warning people of a series of online meetup gunpoint robbereis in Groveland Park and Oakland.
At least 36 people were wounded in shootings across Chicago this weekend, including an armed person who was fatally shot by police early Monday in Little Village on the Southwest Side.
A 75-year-old woman died Tuesday after being injured in a fire months earlier in Oakland on the South Side.
Allen Brown allegedly choked a 35-year-old ride-share driver while trying to steal his vehicle about 9:10 p.m. Wednesday in the 3500 block of South Cottage Grove Avenue, Chicago police said.
In each incident a man, driving a late model black Jeep Cherokee SUV, pulled up alongside a woman waiting for public transportation, showed a handgun and demanded her belongings, Chicago police said.
A robber approached a man in the hallway of an apartment building on Chicago's South Side and shot him in the abdomen.
Chicago police are warning people in the South Side neighborhoods of Oakland and Douglas to watch out for robbers. Three people have been victimized so far.
Authorities are warning residents about a group of carjackers that has been stealing vehicles at gunpoint this month in Kenwood, Grand Boulevard and Oakland on the South Side.
A 19-year-old man was shot to death Saturday in the Oakland neighborhood on the South Side.