The “Windy City Tour,” featuring Rock & Roll Hall of Fame and multiple Grammy Award-winning band Chicago, breezed into Blossom Music Center on Wednesday, August 5. The legendary group is celebrating its 59th consecutive year of touring, a remarkable milestone for a band that continues to fill concert venues with the unmistakable “Chicago” sound that has defined generations.
For me, however, this concert was more than another chance to see Chicago live. I have seen the band perform numerous times over the years, but this night brought back memories of one of my earliest Chicago concerts—August 10, 1971, right here at Blossom Music Center, during the band’s fifth year of touring. That concert became one of the most memorable events in Blossom’s early history. The show was sold out, the roads and parking lots were overwhelmed, and even the band itself had difficulty making it into the venue. The concert finally got underway sometime after 10:00 p.m., an unusually late start that only added to the excitement and chaos of the evening. Fifty-five years later, Chicago was back on the same stage, and I was there once again.
Chicago has certainly earned its place in music history. The band was inducted into the Rock & Roll Hall of Fame and has received multiple Grammy Awards. Great songwriting has always been one of the key ingredients in an artist’s or band’s longevity, and Chicago has certainly benefited from having such talented writers within its ranks.
Two of the band’s original members, Robert Lamm on keyboards and James Pankow on trombone, were instrumental in writing many of Chicago’s most memorable songs. Peter Cetera, the band’s original lead singer and bassist, also contributed to its remarkable catalog. It would be impossible to talk about Chicago’s musical legacy, however, without mentioning the late Terry Kath, the band’s original lead guitarist. Kath’s innovative and powerful guitar work, perhaps most famously heard in his explosive solo on “25 or 6 to 4,” brought a distinctive rock and jazz-fusion element to Chicago’s sound. His playing remains one of the reasons the band’s music continues to sound fresh and timeless more than five decades later. If you have never heard “Free Form Guitar,” it is well worth a listen. It is another example of just how innovative Kath was as a guitarist. Even Jimi Hendrix was reportedly impressed by Kath’s playing after seeing Chicago perform at the Whisky a Go Go in 1968. That is quite a compliment coming from one of rock’s most influential guitarists—and a fitting reminder of just how extraordinary Terry Kath’s talent was.
Fast forward to present day, the current touring lineup continues that musical tradition with a group of talented musicians who not only play their individual instruments but also contribute vocals and harmonies. This combination is an important part of the complex Chicago sound.
While Chicago’s legacy was built by its iconic founding members, the band’s current lineup demonstrates that its signature sound is in capable hands. Today’s ensemble features Justin Avery on keyboards and vocals, Tony Obrohta on guitar and vocals, Nick Lane on trombone, Walfredo Reyes Jr. on drums, Ray Herrmann on saxophone {READ CLEVEROCK’S 2025 interview}, Lee Loughnane on trumpet and vocals, Ramon “Ray” Yslas on percussion, Carlos Murguía on keyboards and vocals, Eric Baines on bass and vocals, and Rudy Cardenas on lead vocals. Together, this new generation of musicians carries Chicago’s distinctive blend of rock, jazz and brass into the future while honoring the sound that has made the band a lasting force in music.
Loughnane is the only original band member currently touring. (Robert Lamm and James Pankow remain active members of Chicago’s legacy and are still important to the band’s songwriting history, but they are not part of the current touring lineup.)
The current musicians are the same group that appeared at MGM Northfield Park Center Stage last November, with the addition of new lead vocalist Rudy Cardenas for this performance.
The harmonies provided by many of the members are another important ingredient in Chicago’s distinctive sound and, like great songwriting, are part of what has helped the band remain successful for so many decades.
The concert opened with “Introduction,” the first song on Chicago’s first album, ‘Chicago Transit Authority,’ released in April of 1969. It was a perfect way to begin the evening. The song is a classic example of Chicago’s multi-faceted jazz-rock sound and the musical experimentation that helped set the band apart when it first emerged.
“Introduction” immediately showcases the combination of rock, jazz, horns, percussion, guitar, and vocals that would become the foundation of Chicago’s sound. Hearing it performed live more than five decades after its original release was a reminder of just how adventurous the band was in its early years.
The audience was a lively mix of younger and “elder” concertgoers, and everyone seemed thrilled to be there. They knew the words to the songs, singing along, dancing, clapping, and cheering their way through one favorite after another. It was one of those concerts where one could look around the venue and see people of different generations enjoying the same music together.
One of the most entertaining moments came during the percussion section incorporated into the Spencer Davis Group classic “I’m a Man.” Reyes Jr. and Yslas each took a turn performing individually before joining together in an increasingly energetic percussion exchange. Adding another layer of difficulty they switched positions while continuing to play flawlessly. The crowd went wild with enthusiastic cheers and applause.
The musicians were clearly having fun playing, and that enthusiasm continued throughout the evening. There was an energy coming from the stage that made its way into the audience, whether you were sitting underneath the pavilion or spread out across the lawn.
The rest of the evening was a selection of music covering roughly the first 15 years of Chicago’s career, with songs chosen from many of the studio albums the band recorded during that period. Chicago has released a remarkable 35 albums, with ‘Chicago XXXV‘ being released in 2022. With such an enormous catalog of music, there is certainly no shortage of songs from which to choose.
And then came the encore: “Free,” followed by the Chicago II classic “25 or 6 to 4.” That was the moment everyone was anticipating, and somehow it remains just as exciting as the first time you hear it. The horns, guitar, rhythm section, and vocals all come together in a way that is unmistakably Chicago. After nearly six decades, the song still has the power to bring an audience to its feet.
The stage at Blossom is very large, and all ten members of Chicago made full use of it. The house sound was superb, running at a slightly lower level in the pavilion than some other rock bands. That worked especially well for Chicago, allowing the many different instruments to maintain their individual clarity rather than becoming lost in the overall volume.
A huge video screen across the rear of the stage displayed, among other things, still photographs of the Chicago musicians from the band’s vast collection of performances over the years. The images served as a visual reminder of just how much history was represented on that stage.
The night couldn’t have been more perfect. Whether you were seated under the pavilion or spread out across the lawn, the music of Chicago seemed to fly through the warm summer air, bringing with it that familiar anticipation you feel every time you see this legendary band perform. The musicians were enthusiastic about playing, and that energy never let up throughout the entire evening. And of course nothing beats the Blossom Music Center venue on a warm summer night.
And for me, there was something else that made this night particularly special. Standing at Blossom in 2026 and watching Chicago perform, I couldn’t help but think back to that August night in 1971 when I first saw them here. Fifty-five years had passed, but the music still had the same ability to bring people together.
The band has changed. The members have changed. The years have certainly changed. But the music of Chicago remains. So cool. So amazing. Chicago style.
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