The most recent was Sunday morning at a store near 87th Street and Langley Avenue in the city's Chatham neighborhood.
At least five businesses were hit over the weekend.
Police say the thieves were armed, and stole bottles of liquor and cash registers.
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CPD also said the suspects will typically break the front glass doors of businesses using stolen vehicles. They have rammed the doors, or used a chain to force open the door using the vehicles.
They're described as seven to eight male suspects, wearing face masks, dark clothing and gloves.
There have been at least nine incidents over the last several weeks.
Incident times and locations include:
- 8000-block of South Kedzie Avenue at 3:05 a.m. May 27
- 800-block of West 87th Street at 4:19 a.m. May 27
- 10000-block of South Western Avenue at 2:45 a.m. June 14
- 9000-block of South Ashland Avenue at 5:15 a.m. June 14
- 400-block of East 103rd Street at 2:55 a.m. June 15
- 200-block of West Root Street at 4:30 a.m. June 15
- 7900-block of South Exchange Avenue at 5:30 a.m. June 15
- 1600-block of East 79th Street at 6 a.m. June 15
- 700-block of East 87th Street at 12:30 a.m. June 16