For Jupiter House Band, the Windy City represents a nostalgic connection.

The Detroit indie-pop collective instantly travels through space and time to revisit past heartbreak on their latest breezy single, “Chicago.”

“I went on a trip to Chicago with a very important person in my life a few years ago. It’s not about that trip; it’s about that relationship,” said Issac Burgess, Jupiter House Band’s vocalist, songwriter, multi-instrumentalist and producer.

“It’s an honest song about a lot of internal struggles and just trying to cope with a lack of somebody you’re used to having in your life.”

Throughout “Chicago,” a ripple of soft drums, glistening cymbals, scintillating electric guitar, subterranean bass and tweeting synths blow across the mind’s universe and yearn for lost love.

Burgess dreamily sings, “Can’t keep feeling down/Ya turned my heart around/And now I feel like a fool.”

“I’m such a sucker for love songs, but I’ve always been self-conscious about writing them. This is my take at a bit of a love song … kind of a breakup song,” he said. “I wrote it when I was 23, and I’m almost 25 now. I think it will mean a lot to other people.”

After visiting “Chicago,” Jupiter House Band shifts their musical orbit to “Feel Like (Wow),” an upbeat, funky ode to maximizing time and setting boundaries.

Infectious waves of pulsating synth, eager drums, jittery bass and curious electric guitar immerse Burgess in long-awaited relief.

Alongside those “Feel Like (Wow)” sighs of relief, Burgess sings, “Can’t keep what’s goin’ on/Or keep from knowin’ how/Your scent on my Oxford shirt/Makes impression how/Makes me feel like wow/I can’t help but think of her.”

“I’m reaching a point in my adulthood where I just can’t give my time and my energy to everyone all the time. That doesn’t have to be a bad thing either,” he said.

“In the past, people have gotten upset, and even I have gotten upset, when you couldn’t reach someone all the time, or you couldn’t be with someone all the time. You could chalk that song up to having a general consensus of not wanting to waste time with drama, gossip or talk.”

The Best of My Love

Jupiter House Band continues to find personal catharsis on “My Love,” a soulful flashback to lost relationships and lingering heartache.

Buzzy organ, emotive bass, thumping drums and divine electric guitar encircle Burgess as he sings, “Never said shit to me, and now she’s gone away/And I don’t know how to feel about it/Well, it’s been about a year now, and I don’t know what to say/I guess this is living life without ya.”

“As of late, that was a way to heal and vent and move past some of those things. It was about eight months into the pandemic, and I took a small vacation. The company that I work for has a cabin in Cadillac, and I took all of my gear into a car and drove up there for a week,” he said.

“I set up all this gear in the living room, and I woke up every day and tried to write and record. I left with two songs, but ‘My Love’ was the only one I felt I could work with.”

Jupiter House Band also works with a passionate rendition of the Eagles’ 1979 hit, “I Can’t Tell You Why,” which channels Timothy B. Schmit’s somber vocals.

Despondent organ, ambivalent synth, clicking drums, tingly cymbals, haunting bass and lonesome electric guitar comfort Burgess as he sings, “Look at us baby, up all night/Tearing our love apart/Aren’t we the same two people/Who lived through years in the dark?”

“I’m a ride-or-die-hard Eagles fan … they’re like my guilty pleasure now. When my dad and I moved back to Oxford in 2009, we listened to the Eagles and Led Zeppelin. That reminds me of my teenage years,” he said.

“During that period, I didn’t listen to their poppy songs. Then, they put out a documentary on Netflix … I watched it and was like, ‘Whoa, the Eagles are so good, and they have so many good songs.’”

The Evolution of Jupiter House Band

Burgess’ musical connection started while growing up in Pontiac. At age seven, he learned guitar and started writing, arranging and performing music.

“I didn’t have the internet as a kid. I had no computer, I had no cell phone, and I had no technology until I was 11,” said Burgess, whose early influences included The Beatles and The Beach Boys.

“My dad has always been the person who’s shown me every record, and I adored that. I wanted to be a rock star as a kid. My dad had the means to buy me a guitar and get me into guitar lessons.”

By age eight, Burgess studied guitar with Ken Andreoni, a Wayne State University jazz masters graduate, at Motor City Guitar in Waterford. He took additional lessons with other instructors over the next five years.

“I started playing in bands, I kept taking lessons and played with younger musicians, and I was in orchestra in school, too,” Burgess said.

Throughout high school, Burgess expanded his musical palette and listened to a spectrum of artists, including Mark Ronson, A Tribe Called Quest, Kendrick Lamar, Bob Dylan and Toro y Moi.

“After I graduated, all of my musical resources went in different directions. Certain people quit playing music, and certain people got in bands and started touring,” he said.

“For me, I had a passion for writing songs, and I wanted to make music that I didn’t have to compromise on. I decided to do it all myself and just make the most out of the situation.”

By October 2016, Burgess moved to Detroit and started writing and recording with his roommates. Those initial collaborations produced two thoughtful releases, the psych-folk Kerchavel EP in 2017 and the psych-pop Baby EP in 2018.

“Both of those were a two-year stretch of coming home every day after work and playing music until midnight or one in the morning,” he said. “We had such a cool party house and such cool neighbors; people were always over.”

In 2020, Burgess started producing EPs for his friends, including Detroit singer-songwriter Emily Parrish. The duo formed Issac & Emily, collaborated with Ian Ruhala, Mike Harrison and Jake Halkey, and released the delectable indie-pop EP, Year in Review, in 2021.

“I think I have my own cool little sound, and I love to apply that to other artists,” Burgess said. “I had a couple of people I wanted to work with before the pandemic, and I started working on a project with Emily at Rustbelt Studios. I’ve done other collaborations before, but that was the first serious one.”

That collaborative instinct also spawned Jupiter House Band, a multi-genre collective of rotating artists and musicians who record with Burgess.

They released their 2020 psych-pop debut EP, Double Planet, which includes timeless covers of The Beach Boys’ “Caroline, No,” and the Grateful Dead’s “Shakedown Street.”

“I’ve always been ambitious to market my own music and my own products, and I’m always bugging everybody to let me help them,” said Burgess, who also released Jupiter House Band’s funky Moonrise EP in 2021.

“I started Jupiter House Band with the concept that I would primarily write the music and record everything, and as people come and go, we would just rotate musicians out.”

Today, Jupiter House Band also serves as an outlet for other creative endeavors, including video production, brand management, cinematography, live shows and more. Known as Jupiter House Detroit, the team features Sam Mead, Max Popkin, Andrew Biggs, John Cottone and Burgess.

“We can also take this model and apply it to other things. The whole idea of Jupiter House is that anyone can help collaborate on this idea. I’m working on a song right now with a friend, and his name is Marek!” Burgess said.

“I love talking to people and connecting with music, and I love collaborating. It’s the perfect way to do all these things together.”

In the meantime, Burgess will book and host Jupiter House Sessions live shows and release new Jupiter House Band material. He’s currently working with Mark Whalen in the studio.

“I’m trying to create a curated music experience on a smaller scale that’s not expensive. We’ve got some cool artists we’re working with, and I’m interested to see where it goes once we get started. I think it will take off on its own,” he said.

“I’d like to get my music out into other states. Right now, most of my audience is in metro Detroit, Michigan and Chicago. I’d like to do one tour before I do a full-length album. Right now, I plan to put out singles, and I’ve got a ton in the works.”