The attackers asked people distracting questions, then punched them in the face before stealing their purses, wallets or cellphones, police said.
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There were three attacks, according to police. The first occurred on Wednesday in the 100-block of South State Street at 11:20 p.m. The second happened on Friday on the 100-block of West Adams Street at 1:25 a.m. and the third a short while later two blocks away on the 100-block of West Van Buren Street.
Police said the three to four attackers were all described as men who were about 18 to 25 years old.
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CTA commuter Jay Hood said he has been robbed at gunpoint before and has advice for people who end up in that situation.
"First thing is you always just give up your items and value your life first," he said.
Police remind commuters to be aware of their surroundings, report suspicious activity immediately, remain calm if confronted and try to remember physical details of the suspect.
Anyone with information is asked to contact Area Central Detectives at (312) 747-8384.