You’ve heard them. Even if you think you haven't, you definitely have. Maybe it was a brassy, punchy anthem during a July 4th barbecue or a synth-heavy power ballad playing in a dentist's office while you gripped the chair arms. Chicago is that rare beast of a band that managed to conquer two entirely different musical universes.
Honestly, the sheer volume of chicago band biggest hits is staggering. We aren't just talking about a couple of lucky strikes. We’re talking about 21 Top 10 singles. They are essentially the American equivalent of the Rolling Stones in terms of chart longevity, yet they often get labeled as "that ballad band" by people who haven't dug into the crates.
The Early Days: Rock with a Mean Horn Section
Before they were the kings of the 80s prom slow-dance, Chicago was a gritty, experimental group called Chicago Transit Authority. They didn't care about three-minute radio edits.
Take "25 or 6 to 4." It’s basically the gold standard for rock songs about writer's block. That iconic, descending guitar riff from Terry Kath? It’s legendary. Kath was a monster on the guitar—Jimi Hendrix once reportedly told the band’s saxophonist, Walter Parazaider, that Kath was better than him.
The song title itself is just a reference to the time of day: 25 or 26 minutes to 4:00 AM. Robert Lamm was just trying to finish a song in the middle of the night. It’s raw. It’s fast. And the horns don’t just sit in the background; they punch you in the face.
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Then you’ve got "Saturday in the Park." Released in 1972, it’s arguably the ultimate feel-good anthem. Lamm wrote it after a trip to Central Park on—you guessed it—July 4th. It captured a moment of pure, unadulterated peace. It hit number three on the Billboard Hot 100 and has stayed on every "Classic Rock Summer" playlist since the invention of the playlist.
When the Ballads Took Over
Things shifted. They shifted hard.
In 1976, the band released "If You Leave Me Now." It was their first number-one hit. It featured Peter Cetera’s soaring, buttery tenor and almost zero of the signature horn-heavy grit that defined their early years. Terry Kath allegedly hated the song. He thought it was too soft.
But the public? They ate it up.
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After Kath’s tragic death in 1978, the band struggled to find its identity. Enter David Foster in the early 80s. Foster is the guy who basically invented the "80s sound." He took Chicago and turned them into a sleek, polished hit machine.
"Hard to Say I’m Sorry" (1982) was the result. It’s a masterpiece of 80s production. It went straight to number one. If you grew up in that era, you couldn't escape it. It was followed by "You’re the Inspiration" and "Hard Habit to Break." Suddenly, the "rock band with horns" was the "band that makes your mom cry."
The Stats Don't Lie
If you look at the chicago band biggest hits by the numbers, the 80s era actually outperformed the 70s in terms of sheer chart dominance, even if "purists" prefer the early jazz-fusion stuff.
- Look Away (1988): Believe it or not, this was Billboard’s number-one song for the entire year of 1989. It’s a power ballad sung by Bill Champlin, not Cetera (who had left by then).
- Will You Still Love Me? (1986): A massive Top 5 hit that proved the band could survive without Peter Cetera's lead vocals.
- Does Anybody Really Know What Time It Is? (1970): The definitive Lamm-led track that established their "jazz-rock" credentials.
What Most People Get Wrong
There’s this weird narrative that Chicago "sold out." People say they traded their souls for synthesizers.
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But here’s the thing: they were always a pop band at heart. Even on their first double album, they were covering "I'm a Man." They wanted to be heard. They wanted to be on the radio. The 80s stuff wasn't a betrayal; it was an evolution that kept them alive when other 60s bands were hitting the state fair circuit.
Also, don't sleep on "Old Days" or "Feelin' Stronger Every Day." These songs bridge the gap perfectly. They have the horns, the rock energy, but also that melodic hook that makes you want to sing along in traffic.
How to Listen Today
If you want to actually appreciate the depth of the chicago band biggest hits, you can't just listen to a "Best Of" compilation and stop after five tracks.
- Start with "Chicago II": It’s a double album. Listen to the "Ballet for a Girl in Buchannon" suite. It contains "Make Me Smile" and "Colour My World." It’s ambitious as hell.
- Watch the 1970 Tanglewood performance: You can find it on YouTube. It shows the band at their absolute peak of live power. No synths. Just sweat and brass.
- Compare the eras: Listen to "Free" (1971) right next to "Stay the Night" (1984). It’s the same band, but the sonic difference is a fascinating time capsule of how American culture changed.
Chicago remains one of the most successful acts in history for a reason. They knew how to write a hook, and they had the musicianship to back it up. Whether you love the funky horns or the weeping keyboards, their impact on the American songbook is permanent.
Next time you hear that opening piano line of "Saturday in the Park," don't just let it be background noise. Really listen to how the bass and horns lock in. It’s a clinic in arrangement that very few modern bands can touch.
To dive deeper into the band's history, check out the documentary Now More Than Ever: The History of Chicago. It doesn't sugarcoat the internal drama or the struggle to stay relevant. It’s a masterclass in rock survival. Then, go back to the discography and look for the deep cuts on Chicago VII—there’s more to this band than just the radio hits.