The crime happened overnight at Nabala Cafe in Uptown.
The owner, Eyad Zeid, told ABC7 this is the second time his cafe has been targeted since he opened over the summer. A similar crime happened last month at the restaurant.
Chicago police confirmed the crimes happened in the 4600 block of North Broadway in the early hours of October 25 and September 2.
Community members joined together Friday to paint murals on the plywood over the windows.
A GoFundMe page has been set up to help the cafe repair the damage.