Shortly after midnight, crews were out in force to tow cars violating the ban.
The ban is enforced on 107 miles of main streets in the city, from 3 to 7 a.m.
It applies even when there's no snow on the ground.
A lot of upset drivers showed up to the city pound lot on Sacramento Monday morning.
"Since I have been here, I have seen 200 cars, at least," Hamid Benhemie, whose car was towed, said.
Frustration boiled over .as tow truck after tow truck pulled into the city tow lot on Sacramento.
Some drivers arriving before sunrise after waking up and seeing their car was missing following the city's winter parking ban going into effect overnight.
"I mean this tow truck is getting three trucks at once," Alonso Bernal, whose car was towed, said. "It is pretty ridiculous."
Donald Jones was able to move his car just in time.
"There's a whole lot of folks that are smart, they got theirs out of here already and they don't have to play this game, wait for the last possible minute to get their vehicle out, or wake up in the morning and find their vehicle no longer here," driver Donald Jones said.
However that was not the case for everyone.
"I had to pay $175 dollars," Jesus Diaz said. "This is a business. This is a way to take money away from Chicago citizens.
"I was downtown, I went to Walgreens and less than 5 minutes. As soon as I came out it was gone," Benhemie said.
For Alonso Bernal, it was a double whammy. He said his car would not be released until his city sticker was updated.
"I found out my car was towed at approximately 1:30 a.m. Monday in downtown," Bernal said. "Unfortunately my city sticker was expired by a month so I have to get a new sticker, to get my car out."
Violators will be towed and ticketed, with a $150 towing fee, a $60 ticket and a storage fee of $25 a day.
Vehicles will be towed to Pounds 2 (10301 S. Doty Avenue or 6 (701 N. Sacramento Avenue).
Residents can visit Chicagoshovels.org for a map of impacted streets and can also call 311 to find out of their vehicle was towed.
The winter parking ban is in effect through April 1.