Two burglaries happened near Diversey and Leclaire avenues, one on Sunday, and the other on Wednesday.
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A business near Fullerton and Keeler avenues was also targeted on Wednesday.
El Taconazo restaurant was one of the businesses damaged.
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All the incidents took place while the businesses were closed, and the suspect gained entry using a cinder block to smash windows.
Once inside, the suspect rummaged through the businesses, taking cash, cash registers and food items.
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Chicago police said no arrests have been made.
The suspect is described as male; 5-feet, 6-inches to 5-feet, 7-inches tall; and wearing a yellow ski cap and brown jacket.
Anyone with information is asked to call the Bureau of Detectives - Area 5 at (312) 746-7394.
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