Originally launched to provide a respite for musicians and audiences alike amid pandemic shutdowns, the Live on Logan outdoor music series continues to make jazz accessible to all. Founder Sergio Castro said he hopes the series can help make Logan Square a jazz destination.
Catch the series’ 2022 closing session Sunday, Sept. 25, at 1 p.m. in Palmer Square Park (2200 N. Kedzie Ave.).
Castro, a longtime Logan Square resident, created Live on Logan in July 2020, after the COVID-19 pandemic had forced the world to go dormant in March 2020. With music venues shut down throughout the city and gig musicians out of work, Castro offered a lifeline in the small, socially distanced jazz concert series outside his home, on Logan Boulevard.
“Everybody was worried about stages and venues, but nobody was really paying attention to the people that it affected: musicians,” Castro said. “There’s a lot of bands out there, but the jazz guys are the ones who do it for a living.”
The series started out on a hand-built stage in Castro’s front yard. The first show, which featured local guitarist and music educator Bill Brickey, drew a crowd of 25 people, Castro said.
Brickey’s “Wiggleworms” set, a series of children’s songs based on a class he teaches at the Old Town School of Folk Music, helped draw that first crowd, Castro said. “He started playing, and people started trickling in … at first, it was a couple of moms and their kids. Then, he broke into his Wiggleworms set, and then more kids started showing up and adults started showing up.”
A Popular Pandemic Respite

At first, Live on Logan ran every week, Friday through Sunday, until a neighbor complained.
Still, Castro said the neighbor recognized the event was for a good cause, and the two agreed to make it a-once-a-week event, occurring every Sunday. “She was empathetic to my cause,” Castro said.
Despite this minor hiccup, Castro said audiences continued to grow as the shows went on.
“When people started coming out, it was 10 at first, then 20, then 30, 40, 50,” he said. “I think there was at one point over 250 to 300 people out on the parkway on Logan Boulevard as it progressed through the summer of 2020.”
Still Going Strong After the Shutdowns
At the start of 2021, the series moved to a bigger venue, transitioning to Palmer Square Park with the help of the Palmer Square Park Council, Castro said.
He described his attitude toward programming as maintaining a balance between showcasing genres he enjoys and exploring diversity from across the jazz idiom.
Thanks to this mindset, some of the most creative artists at the forefront of the genre have graced Live on Logan’s stage. From the thunderous drumming of Jeremiah Collier to the more hip-hop sounds of the J. Davis Trio and the more modern, straight-ahead jazz sounds of saxophonist Chris Greene, Live on Logan has treated audiences to a full spectrum of jazz musicians.
The wide-ranging demographics of the audience reinforce jazz’s unique ability to touch people from different backgrounds, Castro said. And even long after the city and indoor music venues opened up again, the event still makes jazz accessible to a wider audience, he added.
In one show from earlier in the 2022 concert season, Castro said, “I noticed a little girl with her father just kicking back and having a great time, and then I saw an elderly person in a semiwheelchair come out and watch. It made me feel really good about it that they have a place to go. Not everybody can go to a jazz club and take in what I think are the world-class musicians of this city.”
Castro said the demographics of Live on Logan’s audiences echo the diversity of the music on its stage. Guests have come from as far as northwest Indiana, as well as Evanston and other Chicago suburbs.
“Parents with their kids came out, the elderly came out, hipsters [and] nonhipsters came out,” Castro said. Early in the pandemic, “we were the only game in town, to be perfectly honest. There were a couple porch concerts here and there, but I think that [concertgoers] recognized that this had a little more of an organized feel to it.”
A Long-term Addition to Logan’s Outdoor Lineup
This year, Live on Logan has taken place every Sunday from 1 p.m. to 3 p.m., with one group featured at each show. Castro said Live on Logan serves as a great complement to other weekend events in the neighborhood.
“I think people in the Palmer Square area really like the fact of going over to the Farmers Market, picking up a few apples, or picking up something from the [nearby] Puerto Rican restaurant … [to] picnic in the park,” Castro said. The Logan Square Farmers Market (3025-3113 W. Logan Blvd.) continues this season through Oct. 30. Dining options near Palmer Square Park include Puerto Rican spot La Bomba (3221 W. Armitage Ave.) and Cuban eatery Tropicuba (3000 W. Lyndale St.).

Throughout Live on Logan’s first two seasons, the series used a tipping-based model to compensate musicians. Organizers walked tip buckets through the crowd, and guests gave what they could. Castro said a lot of shows pulled in $500 to $700, but he has also seen as much as $1,400.
However, as part of Castro’s desire to make Live on Logan a “truly free” event for concertgoers, the series secured a sponsorship with help from the Palmer Square Park Council. That funds a minimum payment of $750 to each group’s bandleader and a $250 rainout fee.
Early events included digital tip jars. Photo: Alex Shur.
Castro added that the events still welcome tips and that 100% of proceeds go directly to the musicians.
But the series organizer said that he still aims for more. He is seeking grants through the Chicago Department of Cultural Affairs and Special Events to cover expenses, such as a better-quality stage and increased musician pay.
Castro added that he wants to raise Logan Square’s profile in the jazz scene, making the neighborhood the next Hyde Park.
“I think there’s a place for jazz in Logan Square,” he said. “Everybody knows there’s a Hyde Park Jazz Festival. I want to put Logan Square in that space, because it really needs it.”
Guitarist Mike Allemana and his group The Regulators close out the 2022 concert season on Sunday at 1 p.m.
Featured photo: The early days of Live on Logan, on Logan Boulevard at the beginning of the pandemic. Photo: Alex Shur
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