Kentrell Brown, 26, is accused of pulling out a gun and forcing the victims back into their homes.
The crimes happened at two different houses.
The first incident happened in the 6200-block of South Kolin Avenue in West Lawn about 1:25 a.m., police said.
Someone in the house had a gun and a Concealed-Carry License, and there was a shootout. No one was hurt.
The second incident happened about 15 minutes later and less than 2 miles away in the 3300-block of West 59th Place in Chicago Lawn.
Brown has been charged with three counts of armed robbery, one count of home invasion, one count of vehicular hijacking and one count of armed kidnapping.
During a court appearance Saturday, a judge decided Brown would be denied pre-trial release.
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