After Wilson's first gas giveaway last week created gridlock across the city, a larger one took place Thursday.
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This time, his team intended for their second event to operate more like carefully choreographed charitable chaos.
"I had no idea that it was going to be this big," Wilson said, "but when it happened, it just exploded. And I was surprised like everybody else."
And it seemed smoother than last week's.
Cars were supposed to begin lining up at 7 a.m. at 21 locations in Chicago, but not before, the Office of Emergency Management and Communications said Tuesday.
WATCH: Hundreds of cars line up for Chicago-area free gas giveaway
Hundreds of cars line up for Chicago-area free gas giveaway
However, on the North Side, some cars had already begun to line up by 4:30 a.m., and the line only grew as the morning went on.
Some arguments could be seen breaking out before the gas had begun to flow.
"There's people down the block that have been here for a couple of hours, and they come and they cut in -- like it's not fair, so I don't know what's going on," Francisco J. Guevara said. "I'm amazed there's not a fight breaking out yet."
Each car could receive up to $50 in free gas, and each station said it would take in up to 400 cars. Stickers were to be handed out to indicate position in line.
"This time, the volunteers are going to hand out numbers from 1-400," said Khalil Abdullah, the owner of multiple participating gas stations.
Chicago police officers were set up throughout the city to help with traffic control.
"Lineup will begin at 6 a.m. No one will be allowed to enter the lines prior to 6 a.m. If you are there earlier, you will be asked to leave," Cicero Police Chief Jerry Chlada said.
By 7 a.m. in Cicero, hundreds of cars were lined up.
"I was here since 2:50 going around trying to find my spot and thank God I made it," said Norma Padilla, who was first in line in Cicero.
While waiting in line for the free gas, Miss Young ran out.
"Ran around, ran around, beating the lines, and we ran out of gas," Young said.
So, police officers helped push her right to the pump. When Wilson heard about her situation, he offered her more gas and even gave her some cash.
It's his way of giving back to a community he loves so much.
"It's a need out here; people need money to get to work to get to the daycare center, you know, people need money to buy food, you know, somebody has to do something," Wilson said.
Wilson even helped volunteers pump gas.
But last week's giveaway of $200,000 in free gas caused massive gridlock in the city.
Willie Wilson gives away $200K in free gas
Thursday's giveaway also included several locations in the suburbs -- 48 locations in all.
From Cicero to Oak Lawn and areas all across Chicago, the lines were massive, and things didn't go smoothly everywhere.
The pumps broke at one location. Some drivers realized how hectic the last giveaway was and made sure to arrive early and wait.
"Some people here from 5 o'clock, that's why I feel bad, and a lot of people no gas," said gas station owner Yousef Shiek. "I just give the lady $15 from my own pocket to go across the street."
"I had my son actually behind me, and he was not a trooper like me so he left, went home, and I'm here," Sally Sarpelli said.
Donald McGill attempted to get gas last week, and waited for hours.
"We were right at the gas station; we didn't even get gas," he said.
But he did make it Thursday, just in time.
"Right now I'm just happy I'm here; I'm about to run out of gas!" McGill laughed.
Park Forest police said they would be directing cars through a residential area to avoid backup on the major thoroughfare.
"We found out about it Saturday afternoon so it's been kind of a rush to get things prepared," said Deputy Chief Paul Winfrey with the Park Forest Police Department. "It took the better part of the day to try and figure out the best route that will cause the least amount of impact to residents and businesses."
The town of Cicero and the Chicago Police Department were also working with Wilson to mitigate traffic issues this time and ensure public safety.
"Last week, we really weren't given much notification. This time around, we had a few days extra to plan for this," said Rich Guidice, executive director for the Office of Emergency Management and Communication.
"All side streets south of Cermak Road, between Lombard and Laramie Ave., will be closed beginning at about 3 a.m.," Chief Chlada added.
A spokesman for Wilson said they had "a few" suburban locations decide not to participate Thursday "for their own reasons."
Those locations include Alsip and the Thorntons in Bellwood and Dixmoor.
The Posen Police Department posted to its Facebook page saying the gas giveaway is canceled there, as well.
SEE MORE: Chicago free gas giveaway: Businessman Willie Wilson offering $200K in fill-ups across city
With prices well above $4 a gallon in some places, Thursday's giveaway was something of a lifeline.
"I just got to give back; you know it's hard times right now. Everybody is going through something, so it makes me feel good," volunteer Lenora Williams said.
The stations also lowered their prices, so more people could partake, Wilson said.
He added that if prices stay high, he'd be willing to do another giveaway.
WATCH: Willie Wilson talks about Chicago free gas giveaway
Chicago businessman Willie Wilson gives update on gas giveaway
Participating Gas Stations: Free Gas Starting at 7 a.m. Thursday until $1 million is exhausted
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Austin
Shell at 6129 W. North Ave., Chicago
South Austin
Citgo at 5103 W. Madison Ave., Chicago
Citgo at 5150 W. Chicago Ave., Chicago
Rogers Park
Amoco at 7201 N. Clark St., Chicago
Gage Park
Shell at 5230 S. Western Ave., Chicago
Washington Park
Super Save at 48 E. Garfield Blvd., Chicago
Humboldt Park
Citgo at 1345 N. Pulaski Road, Chicago
Fernwood
9901 S. Halsted St., Chicago
East Garfield Park
Marathon at 340 S. Sacramento Blvd., Chicago
Roseland
Super Save at 11100 S. State St. Chicago
9452 S. Cottage Grove Ave., Chicago
Park Manor
Citgo at 6700 S. Cottage Grove Ave., Chicago
Grand Crossing
BP at 7600 S. Chicago Ave., Chicago
North Center
BP at 3955 N. Western Ave., Chicago
Lawndale
Amoco at 4401 W. Roosevelt Road, Chicago
The Gap
BP at 342 E. 35th St., Chicago
Garfield Ridge
Shell at 6434 W. Archer Ave., Chicago
West Elsdon
BP at 4401 W. 55th St., Chicago
Gresham
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Clark at 1201 W. 87th St., Chicago
Canaryville
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Cook County
North Suburbs
Mobil at 1950 Green Bay Road, Evanston
Phillips at 9340 Irving Park Road, Schiller Park
Mobil at 9401 W. Higgins Road, Rosemont
Shell at 2474 Thatcher Ave., River Grove
Shell at 4555 N. Nagle Ave., Harwood Heights
West Suburbs
Super Save at 101 W. Madison St., Maywood
BP at 11201 W. Cermak Road, Westchester
BP at 5201 W. Cermak Road, Cicero
Amoco at 1700 N. Mannheim Road, Stone Park
Mobil at 1101 N. La Grange Road, La Grange Park
BP at 17th Avenue and Bataan Drive, Broadview
Shell at 3901 S. Harlem Ave., Stickney
BP at 1309 N. 25th Ave., Melrose Park
BP at 1600 Oak Park Ave., Berwyn
South Suburbs
Falcon at 18280 S. Pulaski Road, Country Club Hills
Citgo at 13801 S. Halsted St., Riverdale
Exxon Mobil at 1421 E. Sibley Blvd., Dolton
BP at 15857 S. Halsted St., Harvey
Citgo at 15221 S. Halsted St., Phoenix
BP at 5548 W. 159th St., Oak Forest
Citgo at 11901 S. Marshfield Ave., Calumet Park
Shell at 385 Sauk Trail, Park Forest
BP at 17450 Kedzie Ave., Hazel Crest
GoLo at 4005 W. 135th St., Robbins
Falcon at 8702 S. Roberts Road, Hickory Hills
Shell at 2401 Lincoln Highway, Olympia Fields
Mobil at 431 W. Lincoln Highway, Chicago Heights
BP at 11040 S. Pulaski Road, Oak Lawn