The first break-in happened in Old Irving Park around 2:45 a.m. at Lou Malnati's Pizza and Backlot Coffee on Avondale Avenue near Irving Park Road.
Police said a witness saw two suspects get out of a dark-colored car and break-in to one of the restaurants then forced their way into the other one.
Around 3 a.m., burglars targeted Blaze Smoke Shop in the 1100-blocf of North Western Avenue. Owner Elyse Lopez said it's the seventh burglary the shop has had since June.
"It's been an ongoing thing this summer," she said. "I'm not allowed to put shutters on the windows because it's not a good look to the community."
Surveillance video shows the suspects breaking the business' glass doors with a sledgehammer then entering, grabbing merchandise and leaving in a black car parked on the curb.
Lopez said the damage they left behind cost far more than the inventory stolen.
Half an hour later, a similar scene occurred more than a mile away at Saint Lucia's Smoke Shop in the 2000 block of Western Avenue, also breaking in through glass windows.
Around 4:05 a.m. police said someone broke into a Portage Park Dairy Queen in the 5600-block of Irving Park Road. Officers said a grey car was seen leaving the scene.
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Less then 40 minutes later, Earl's BBQ in the 4800-block of Austin Avenue was also targeted in the Jefferson Park neighborhood.
It is unknown exactly what the burglars took. No injuries were reported. No one is in custody.
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Police have not confirmed which or how many of these incidents may be connected.