Andrew McMahon celebrates Jack's Mannequin's 'Everything In Transit' at Schaumburg drive-in shows

With three critically acclaimed projects - Something Corporate, Jack's Mannequin and Andrew McMahon In the Wilderness - making up the bulk of his two-decade career, the odds seem likely you've stumbled across Andrew McMahon's distinct vocals and radio-friendly, piano-driven rock somewhere.

But wherever you know him from, Chicago-area fans can see McMahon bring his engaging depth and stage-show flourish to these trying times with the “Drive-In Through a Dream Tour,” coming to Schaumburg's Boomers Stadium for three parking lot shows this weekend.

“Who knows why I have this instinct to continually burn down what I've built and start over again,” McMahon said of his various projects during a recent phone interview, “but it's made me feel really fortunate to be introduced to so many different people at different stages of their lives.”

The tour is a celebration of the 15th anniversary of his Jack's Mannequin debut release, “Everything In Transit.” Songs from the album will be played top to bottom, along with selections from his bookend bands as well.

“The record as a whole and the experience of my early 20s and stepping out on my own after Something Corporate - which I was in since I was a junior in high school effectively - I think 'Transit' really transmitted that experience pretty successfully,” McMahon said. “And that it's a fan favorite certainly makes it easier to want to go out and celebrate it with the people who loved it.”

“On the flip side,” he continued, “it was the genesis of the (Dear Jack) foundation, and it was a precursor to a really strange and dramatic time in my life, having gotten sick around then. And it also is the love story to my now-wife, and chronicles our breakup and getting back together. So there's a lot of deep, really personal history that's wrapped up in the album itself.”

After beating acute lymphoblastic leukemia in his early 20s, McMahon formed the Dear Jack Foundation, a charitable organization dedicated to raising money for supporting patients and survivors of adolescent and young adult cancers. His visit to the suburbs comes on the heels of sold-out drive-in gigs in California and New Jersey earlier this summer, one of which was livestreamed, raising nearly $80,000 for the charity.

McMahon's drive-in tour this weekend will adhere to Illinois public safety guidelines, requiring guests to wear masks and stay in the space around their socially distanced parking spaces.

“We put our heads together to see what can we do and how can we do this safely so we're not part of the problem,” he said. “To give people a chance to be entertained in a time that amounts largely to puzzles and Netflix.

“It's a strange way to view a concert, but walking away from the first one it was nice to be able to engage and do something in the middle of the craziness. It felt like a release. There's a lot of bottled-up tension, and it's a way to bleed off some of that in a positive way,” he said. “I think at this moment, more than anything, everybody needs a little bit of something good to distract them from a whole lot of uncertainty. And it's been a nice distraction for myself, too.”

McMahon had pulled back on touring the last few years, so he and his band had a big summer of festivals and new music planned for 2020. After getting over the initial concern for his business - helped by the July release of “Get On My Wave,” a single recorded prior to the pandemic lockdowns - he turned his attention to the positives in his life.

“Once I sort of calmed down, I decided to just do what I could to spend time with my wife and daughter and focus on some things that I wouldn't otherwise be able to do if I was back on the road and in the studio,” he said. “I think that helped me reframe my perception of the whole thing.”

Flexing his writing muscles on a book about his personal history scratched a creative itch, but it didn't fill the void that playing live music left. So he's excited to be able to return to the Chicago area for these shows.

“I actually lived in Winnetka for a few years, so I feel very close to the city itself. My dad opened up the Bloomingdales downtown in '88 or '89, so we moved there for a few years when I was young,” he said. “It's a place I certainly feel close to.”

Andrew McMahon's “Drive-In Through a Dream Tour”

When: 6:30 p.m. (gates at 5 p.m.) Friday through Sunday, Oct. 2-4

Where: Boomers Stadium parking lot, 1999 Springinsguth Road, Schaumburg

Tickets: $200-$350 per car of up to six passengers; andrewmcmahon.com/tour