Work began Wednesday in the 6300 block of south Ashland. Mayor Rahm Emanuel was on-site to help kick off the work.
Emanuel said the miles of streets being repaved equal the distance from Chicago to Des Moines, and talked about how badly this work is needed after Chicago's extremely cold, snowy winter.
"Everybody that had to go through winter, this is your day," Emanuel said. "For all of that pain, 345 miles of gain."
The mayor's office also said utility companies are expected to repave 20 miles of streets as part of their infrastructure work.