While many would argue Joe's on Weed isn't exactly a dive bar, Brooks said the point of the tour is to play small venues around the country to get back to his roots and where he got his start.
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Brooks told Windy City Live's Ryan Chiaverini that he's singing about the places that kickstarted his country music career in his newest single.
"I think this is where it was all born," Brooks said. "When you hear 'Friends in Low Places' or "Callin' Baton Rouge,' you can still hear them echoing off the honky-tonks you played in, so this is going to be fun."
The superstar has a storied history with the Second City, and Chicago country fans love them some Garth Brookes.
"I think he makes the fans anywhere feel special. I think he's just that kind of person," said Chrissie Butkus, fan.
"He's very real. He's very human. I don't feel like he takes his stardom up too many levels," said Mary Delucca, fan.
And he loves them back.
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"I'm not from Chicago. I stick out like a sore thumb here, but people have always embraced our stuff here," Brooks said.
There were about 400 people who had tickets to Monday night's show at the Lincoln Park venue, all of which were won through contests and raffles from local country music radio stations. One woman said she called into stations 1,500 times and answered 10 trivia questions to win her tickets.
"I mean, you're close. It's somebody who's selling out stadiums all over the country and you can see him in front of a few hundred people. It just changes the whole perspective of everything and I want to be a part of it," said Nate Kinsey, fan.
And alongside his original honky-tonk band, Brooks planned to give the fans what they came from.
"There's fun and then there's stupid fun and whatever is after that is what this is going to be," he said.
The remaining six cities on the dive bar tour have not yet been revealed.