Styx and Chicago Brought Their Windy Cities Tour to St. Louis for a Night of Classic Rock

August 26, 2026 Sean Derrick

Styx performing Monday at Hollywood Casino Amphitheater in St. Louis. Photo by Sean Derrick/ Thyrd Eye Photography.

–by Tom Schmidt

–photos by Sean Derrick/ Thyrd Eye Photography

If you were looking for a concert that had a variety of instrumentation, great harmony singing some great classic rock songs, with new music and great stage presence, then the only way to top that would be with a double billing. That is exactly what I got on August 24^th at Hollywood Casino Amphitheater in St. Louis. Concertgoers were treated to Chicago and Styx co-headlining a concert called “The Windy Cities Tour”, since both bands originate from Chicago. The tour started back in February with a limited residency at The Venetian Theater at the Venetian Resort in Las Vegas.

Chicago performing Monday at Hollywood Casino Amphitheater in St. Louis. Photo by Sean Derrick/ Thyrd Eye Photography.

Chicago was the first to perform. Their iconic horn section is still amazing. Sadly, the only original member of the band is Lee Loughnane, the trumpeter. He still has the chops to play all of the music and performed masterfully on Monday.

Loughnane played a trumpet and flute duet with Ray Herrmann playing the flute. Throughout the set Hermann performed on many instruments including the soprano saxophone, tenor saxophone, and the flute. Meanwhile, Loughnane occasionally traded in his trumpet for a flugelhorn (when he wanted a more mellow sound) and a cornet.

Not to be outdone, Nick Lane showed off his skills on the trombone, and, at one point the whole slide accidentally (?) slid out. I’m not sure if that was on purpose for show, but it certainly caught my attention.

The lead vocalist, Rudy Cardenas, is the newest member of the band and has only been with them since May! He did a great job working with the audience and with great range performed the songs beautifully. Speaking of singing, different members of the band took turns leading the different songs while all harmonized well with each other. Not to be outdone, the rhythm section was great backing up the horn section when needed, and did a great job when it was their turn to lead.

During a solo of the percussion section, (with drummer Wally Reyes Jr. and percussionist Ramon “Ray” Yslas) traded spots during the solo. One would keep playing while the other walked over and took over the beat while the other one walked to the other station. What a great way to highlight them!

After an intermission, Styx came out for their set, opening up with “Fooling Yourself (The Angry Young Man)”. The song opens with the great keyboard work of 27-year Styx veteran Lawrence Gowan (more on him later). I’m not much of a lighting person, but when the group performed the song “Lady”, the stage was darkened except the keyboard, while the drummer, Todd Sucherman, played a tambourine and finger cymbals on beats 4 and 1. Different parts of the drum kit lit up in time with those two parts, which was impressive.

They played a song off their latest album Circling From Above called “Build and Destroy”. It may be new, but it has all the elements of a classic Styx song; featuring a strong keyboard part with great harmony and guitar. Gowan mentioned that the song “Crystal Ball” is 50 years old this year, yet it doesn’t feel that old.

Vocalist/guitarist Tommy Shaw introduced that song by explaining that when he wrote that song, he decided to write it for a 12-string guitar. He said he wasn’t sure why but decided to write it that way. A couple of songs later, the band gave him trouble about the song, “Our Wonderful Lives” being written for a banjo, to which Shaw pulled out the banjo and proceeded to start the song.

To close out the set, Gowan mentioned that they were going to perform an “old sea shanty” and wanted the audience to sing along, of course, it was “Come Sail Away”. Two days earlier, I had interviewed Lawrence Gowan, and he talked about the keyboard he uses and how he ends the Bridge section with the keyboard solo by playing a hand over hand descending chromatic scale. I watched him, and what do you know? That’s exactly what he played! The band finished with two encores, “Mr. Roboto”, with the band staring at guitarist James “JY” Young acting like they were wondering if he was a robot and “Renegade”. The band really has a good rapport up on stage. They almost have to since Lawrence told me they do about 100 concerts per year.

Both groups are giants and legends in the rock genre. They both have a huge library of hits. They also keep their fans engaged for a memorable evening and experience.

Check out the full gallery of photos after the setlist below.

Chicago Setlist:

Dialogue (part I and II)

Alive Again

If You Leave Me Now

Make Me Smile

So Much to Say, So Much to Give

Anxiety’s Moment

West Virginia Fantasies

Colour My World

Now More Than Ever

Does Anybody Really Know What Time It Is?