All five incidents happened near Wrigley Field. In each case, victims were forced into a car, robbed, then kicked out of the car.
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"There's a lot of eyes, a lot of cameras, a lot of light on Clark Street," said Sam Sanchez, owner of Old Crow Smoke House. "Clark Street they shouldn't take lightly, because we're pretty organized over there."
Chicago police said three of the incidents happened between midnight and 1:15 a.m. Saturday and Sunday along the 3400-, 3500-, and 3600-blocks of North Clark Street, as well as the 1100-block of West Addison. The fifth incident also happened in the 1100-block of West Addison, police said.
Police said the men in question forced the victims into a gray sedan at gunpoint and robbed them of their cellphones and wallets, before kicking them out of the car.
SEE ALSO | Woman escapes attempted kidnapping in Chicago's West Loop, police say
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In the West Loop, Katalin Rodriguez Ogren is teaching free self-defense classes after a series of attempted kidnappings there last month.
"At the end of the day, when you're being attacked, you're in a fight. You've been ambushed, it's not something you've planned for," she said. "Personal safety management is something that's important just like personal finances and personal health."
She said being able to defend yourself is a critical skill set that boosts confidence.
There are two more free self-defense classes happening this month at POW! Gym in the West Loop on Saturday and the following Monday. Click here to sign up.