Either way, victims of the boot believe it's unfair.
The city has alerted more than 60,000 motorists that they are eligible for a boot. For hundreds of other motorists, it's already too late.
"I went out to get my car on Saturday and it was gone. Called the city and it had been booted and towed," said Will Richards.
"I got notified by a co-worker I got the boot," said Harold Watts.
The city is cracking down on motorists with unpaid tickets that are older than 1 year. Under a new policy, all it takes is two and you get the boot. Some alderman say the city has eased it's residents into this new rule by offering a 10-week amnesty program, expanding the city's payment plan, and by limiting the two ticket rule to tickets older than one year.
"You have broken the law, not once but twice. You have been given notice, I'm very sympathetic to tough economic times, but I think people have to number one, not break the law, and if they do take care of business right away," said Ald. John Pope, 10th Ward.
"In these times it's a little difficult, so it is really important for people to know the rules," said Helen Shiller, 46th Ward.
Getting the boot quickly adds up. With towing costs, storage fees and tickets that multiplied in price, Wrigleyville resident will Richards is about to pay more than $1,300 to get his booted car back from the city. Richards and others believe booting is just a way for the city to unfairly make more money.
"The city could use a little extra cash. I don't know if pinching people at every single last resort is the way to do it… but I'm not in charge," said Richards.
"I think it is a scam. Times are hard so you want to make more money by ripping off pockets of the people, where is the justice here?" said Watts.
The revenue department did not say how much the city plans to make with the new policy. For more recent tickets, the law has not changed. Motorists are boot eligible with three tickets that are in final determination status, which means motorists were sent at least four notices for each ticket.