The fire started in the 2400 block of North Mason in the Belmont Cragin neighborhood at around 2 p.m.
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Massive flames and thick black smoke poured from the residential block, as firefighters on ladders attacked the blaze.
Officials said the fire started in one house and spread to others. A total of four houses and a coach house were damaged in the fire.
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Chicago Fire Department officials said one firefighter is being treated for non-life-threatening injuries. No other injuries were reported in the blaze.
Firefighters appear to have put the fire out, and an investigation into the cause is underway.