Video provided by the Patriot Pub and Gaming Parlor at 141st Street and Cicero Avenue shows the damage to the machines.
The owner said the thieves smashed through the front doors and windows around 4 a.m. Thursday.
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Pictures show as many as eight masked suspects then breaking into the machines and stealing money.
This is the second time this month that business has been hit by thieves.
Crestwood police did not immediately provide information on the crime.
This is a developing story; check back with ABC7 Chicago for updates.