Video from the scene showed some people jumping on cars at the BP gas station near 31st Street and Michigan Avenue.
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Chicago police said an 18-year-old woman was struck by a gray vehicle, which fled the scene. The woman was injured in the leg and transported to a hospital in fair condition.
15 arrested in connection with Loop chaos after 2 teens shot near Millennium Park: Chicago police
A gas station attendant said scores of teenagers flooded into the station and ransacked the store and even broke glass above the front door.
Video taken by a gas station clerk shows police officers standing by as young people flooded the streets.
Neighbors nearby where the teen takeover happened last night said these destructive gatherings are embarrassing for the city.
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"It's embarrassing more than frustrating because there is now justifiable reason for it," a man who lives down the street from the gas station said. "We used to have a sense of pride. Now, we've got young people twerking in the middle of the street. Wilding out. Cursing. Running up and down, jumping on peoples' cars, doing all type of ridiculous things."
Dennis Jones picked up the trash left on the street nearby.
"It is embarrassing knowing the young kids are doing this just for no reason," Jones said. "I don't know what they get out of it though. It's fun I guess? I don't get it because I never did it when I was a teenager."
The incident raises concerns about how to best mitigate or control these sudden and sometimes unpredictable gatherings, both in the city and the suburbs.
"You've got to put God first and pray," parent Jamaree Fleming said. "Just try to teach them right from wrong. If you get into trouble, I'm not going to get you out of trouble."
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One of these teen takeovers got out of hand downtown and turned violent in April, when a couple visiting the city was beaten up and robbed near Michigan Avenue and Randolph Street.
The frightening situation was all captured on cell phone video. Two teens were also shot during the gathering and 15 others were arrested.
Tinley Park carnival canceled Sunday after fights break out during teen 'flash mob': VIDEO
Just last month in the south suburbs, a Tinley Park carnival was shut down early after 400 young people gathered during an organized flash mob incident.
Multiple fights broke out and one police officer was injured in the unrest.