Skip to content


Chicago is more than a band; they are a force. Formed in the vibrant city of Chicago, Illinois, back in 1967, this group’s journey has been a breathtaking exploration of genres. Originally known as the Chicago Transit Authority before shortening its name, the band’s self-described “rock and roll with horns” sound defied conventions and pushed boundaries.

A product of the late 1960s Chicago music scene, the ensemble brought together exceptional talents: Peter Cetera on bass, Terry Kath on guitar, Robert Lamm on keyboards, Lee Loughnane on trumpet, James Pankow on trombone, Walter Parazaider on woodwinds, and Danny Seraphine on drums. Their individual skills harmoniously intertwined, with Cetera, Kath, and Lamm sharing vocal duties. Although there have been lineup changes throughout the years, the essence of Chicago has always remained true to form.

With hits like “If You Leave Me Now,” they proved their mettle, earning ten Grammy nominations and winning one for the aforementioned track. Their debut album, “Chicago Transit Authority” (1969), even found a place in the Grammy Hall of Fame in 2014. But that was just the beginning.

Boasting over 100 million records sold worldwide, Chicago’s success is staggering. Billboard named them among the top artists in history, and their albums regularly soared to the top of charts. The group’s album “Chicago” became one of the first rock acts to fill Carnegie Hall for a week, further cementing their status as trailblazers.

Furthermore, Chicago has earned a multitude of accolades, from inductions into the Rock and Roll Hall of Fame in 2016, a spot in the Songwriters Hall of Fame, and the Grammy Lifetime Achievement Award in 2020. Chicago is certainly an unforgettable chapter in the story of rock, one that will be told for years to come.

An Evening with Chicago – Where Timeless Classics Meet Unmatched Talent

A Night You Won’t Forget, Courtesy of Headline Booking

We bring more than 20 years of professional experience in curating extraordinary live events to the table. From your initial inquiry to the moment the final chord fades, we’re here to make your experience as smooth as Chicago’s saxophone solos.

No Stress, All Entertainment

Overwhelmed by the nitty-gritty? Don’t sweat it! We’re your backstage crew, taking care of every tiny detail—from coordinating with Chicago’s management to ensuring all technical requirements are met—so you can sit back and enjoy the show.

The Legendary Chicago Journey

Born in the Windy City in 1967, Chicago has become one of the longest-running and most successful rock bands in the U.S., featuring timeless hits like “If You Leave Me Now,” “25 or 6 to 4,” and “Hard to Say I’m Sorry.” They’ve been inducted into the Rock and Roll Hall of Fame, and they’ve got a sound that blends rock, pop, and jazz, a combo that’s earned them a legion of die-hard fans over the years.


Headline Booking offers a vast catalog of featured artists from around the globe to bring music and smiles to your private party, corporate event, or fundraiser.

Any Questions? We’ve Got You Covered

Curious about Chicago’s availability or performance fees? Want to know more about their stage setup or any special requests they might have? Headline Booking is your go-to source for all your Chicago-related queries.

It’s More Than a Concert; It’s a Chicago Experience!

When you bring Chicago to your event, you’re giving your guests more than just a musical performance. You’re offering them a time-traveling musical journey they won’t soon forget, filled with smooth harmonies, incredible instrumentals, and iconic songs that have stood the test of time.

Book Chicago Today—The Legends Don’t Wait!

Ready to elevate your event with some bona fide rock ‘n roll history? Get in touch with Headline Booking Group today to secure a performance that will have your audience raving long after the lights go down


Book The Beach Boys now for an iconic concert experience with Headline Booking. Contact us for a legendary event!
By John Mathew Smith & -, CC BY-SA 2.0,
Book Ziggy Marley for your next event with Headline Booking – experience legendary music and unforgettable moments. Contact us now!
By Derek Russell - <a rel="nofollow" class="external free" href=""></a>, CC BY-SA 2.0, Link
Book Don Henley for a legendary performance with Headline Booking. Elevate your event to new heights. Contact us today!

Entertainer request

Let’s make your event special. Fill out this contact form and we will get started securing your requested headliner. 

error: Content is protected !!