The young man was caught on surveillance video at a local pet supply store, where a manager said he made off with $180 in cash.
Police say the boy and his mother's 25-year-old boyfriend then hit up about a dozen other businesses on the city's west side.
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"We definitely don't come across 11-year-olds committing these sorts of crimes on a regular basis. It's really unfortunate," a local police spokesperson told WISC-TV.
Authorities eventually caught up with the boy at nearby Walmart. They say he had credit cards that had been stolen from employees of the various stores.