Police said two Uptown-area businesses, including a Chase Bank, were spray painted and had windows broken on North Clark Street between West Winona Street and West Carmen Avenue.
In one case, a smoke grenade was set off. The group of 10 to 15 people then went inside and caused more damage.
The businesses were closed at the time.
The suspects, both men and women, were described as between 18 and 25 years old. They wore dark hooded sweatshirts, dark-colored pants and dark-colored ski masks.
Police asked anyone with information to call them at 312-744-8263.
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