Chicago Fire Department paramedics were transporting a police officer with a significant head injury at about 7:20 p.m. Friday.
A female civilian was also reported with a head injury at about 7:22 p.m. One patient is also in police custody in the ambulance.
More injuries were expected, as ambulances staged near the protest scene.
Illinois State Police also responded to the scene to assist Chicago Police Department. University of Illinois police and US Secret Service agents assigned to protect Donald Trump were also on the scene.
People were attempting to enter the I-290 expressway at Racine.
Interim Chicago Police Superintendent John Escalante said there were five protesters arrested. Two police officers were injured — one was hit in the head with a bottle.
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