Chicago's street sweeping season will begin April 1st and run through mid-November. If a street is scheduled for sweeping, a temporary no parking sign will be posted along the route the day before service to ensure curb-to-curb cleaning. Some arterial streets may already have permanently posted signs that specify a once-per-week period when parking is prohibited due to sweeping.
Residents who need more than one day notice of street sweeping should contact their local ward sanitation office.
More information can be found here.