Short answer: not on your own driveway. Yes if any part of the can sits on the street, alley or sidewalk.
When you need a permit
A dumpster on private property, like a driveway or private lot, does not need a city permit. If any part of the dumpster sits on the public way (the street, an alley or a sidewalk), the City of Chicago requires a permit from the Chicago Department of Transportation (CDOT).
Placing it on the street? The Roll-Off Team can pull the permit for you when you book. [Show only if the client confirms they pull permits.]
How to get one
Apply through the CDOT permit portal before delivery day.
List the address, placement and dates.
Note any parking meters the can will block.
Keep the permit on hand while the dumpster is out.
What it costs
Permit fees are set by CDOT and change from year to year. For 2025, CDOT lists an application fee of $22.05 on a residential street, plus a placement fee of $50 (30 yards or less, outside the Central Business District) for 1 to 3 days. [Verify against the current CDOT fee schedule before publishing.]
Suburbs
Rules in Cook, DuPage and Will County suburbs vary by village. Some require a permit for street placement, and some HOAs have their own rules. Check with your village before booking.
