For musicians to be in a band for over 50 years is an incredible accomplishment, and one that Chicago can proudly claim. This places them alongside other legendary acts such as the Rock and Roll Hall of Famers, where their legacies will continue to be honored and ired even after they stop performing.
The formation of Chicago dates back to 1967. Throughout the span of their career, the "Rock and Roll band with horns" has released 26 studio albums, selling over 100 million records worldwide. This has made them one of the best-selling groups of all time. During the '70s and '80s, they consistently produced hits. They managed to break through during the MTV craze and remained relevant in the 2000s. Identifying the songs that define them is a look at how the band has lasted decade after decade, from the greatest hits to the meaningful ones.
10 If This Is Goodbye
Album: Chicago XXXVIII: Born for This Moment (2022)
Fifty-three years after their first release, Chicago debuted their 26th studio album in July 2022. It had been almost a decade since they released new material, but they were back with a 14-track record. The band wasted no time evoking emotions in their fans as the second song, "If This Is Goodbye," was as poignant as it sounded. They aimed to broach the subject of endings, which was made even more impactful thanks to the music video.
Fifty-three years after their first release, Chicago debuted their 26th studio album in July 2022.
Of course, music videos can sometimes merely serve as a backdrop to a great track, but occasionally they genuinely bring words to life by telling a compelling story. Even if, upon first listen, a Chicago fan thought the song was about something other than the band, the video confirmed its true intent. Essentially, it is a trip down memory lane, reflecting on the band that has been together for over 50 years. It wasn't an easy subject for them to address, but it is one that defines this part of their career.
9 All The Years
Album: Chicago XXXII: Stone of Sisyphus (2008)
The 2008 album, Chicago XXXII: Stone of Sisyphus, may not be the band's most famous, but it has the most interesting story. This is because the album was originally recorded in 1993, intended for a 1994 release, but a conflict with a record company prevented this from happening. Therefore, it became a lost album, held back for years. Eventually, the band regained the rights to the music and finally had the desire to release it.
Given that the album was recorded 15 years prior, some of the subject matter was more relevant to the '90s. This made the track "All the Years" stand out, as it reflected the politics of that time period. This was a statement from the band, asserting that in all the years they had observed, not much had changed regarding politics. It seemed to be the same issues repeating. Surely, it was a divisive subject to write about, but the band approached it when they deemed it necessary.
8 Chasin’ The Wind
Album: Twenty 1 (1991)
After being one of the most consistent bands throughout the 1970s and 1980s, Chicago entered the '90s looking to build on the legacy they had created. They released their 17th studio album in January 1991. Overall, the record performed well, peaking at 66 on the Billboard 200. One of the biggest tracks from it was "Chasin' the Wind." This song ended up on the Billboard Hot 100, marking the 36th time the band had placed on it.
The success the band would see became very important, as the rest of the decade would be tough on them. This is where they would have their lost album due to the record label dispute, which cost them another release. They would put out a studio album in 1995, focusing more on thematic material, but it wasn't as successful as their Top 40 work. They would then focus on Christmas songs to end the decade, marking the conclusion of a time of change and experimentation.
7 I Don't Wanna Live Without Your Love
Album: Chicago 19 (1988)
As the 1980s were coming to an end, Chicago ensured that one more album was released. Arriving in June 1988, Chicago 19 was the band's fifth record of the decade. Commercially, it performed well, thanks in part to two major hits, "Look Away," and "I Don't Wanna Live Without Your Love." There is no denying the success of "Look Away," as it ranked first on the Billboard Hot 100, but there's more to the legacy of "I Don't Wanna Live Without Your Love."
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Through many different genres, some of the biggest names ever in music put out hit songs that have come to define the decade of the 1980s.
Not only did the track place third on the Billboard Hot 100, but it was also featured in the Netflix movie Death Note, which further enhanced the legacy of the song even more. With two more very successful songs to close the decade, Chicago cemented their place as one of the most important bands of the '80s. It was a major accomplishment that they were able to stand out so much, as they competed against some of the biggest names music has ever known.
6 Questions 67 And 68
Album: Chicago Transit Authority (1969)
Every band must begin somewhere, and for Chicago, it all started with their debut single "Questions 67 and 68." It performed excellently for the band, finishing in the 71st position on the Billboard Hot 100. The success of the song helped their first album become a hit. In fact, the song was so important that Peter Cetera, who was the frontman of Chicago for many years, listed it as the ninth best in the band's history.
For Chicago, it all started with their debut single "Questions 67 and 68."
The 1969 release, Chicago Transit Authority, reached as high as the 17th spot on the Billboard 200, making the record an instant hit for the band. Beyond its placement on the charts, it earned them a nomination for a Grammy Award. In 2014, it was even inducted into the Grammy Hall of Fame. Then, in 2025, the Library of Congress selected it for preservation by the National Recording Registry, labeling it as "culturally, historically, or aesthetically significant."
5 Hard To Say I’m Sorry
Album: Chicago 16 (1982)
With the release of Chicago 16 in 1982, the band further cemented their legacy, as it marked their 13th studio album. This firmly placed them above the elusive double-digit release mark, meaning their name would forever be linked to some of the greatest classic rock bands in history. While the significance of the album was impressive, what made it even greater was the band once again had a huge hit song.
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These classic rock bands are beloved because of their hit songs, spaced across impressive discographies that include at least 10 albums.
"Hard to Say I’m Sorry" was the lead single for Chicago 16, which was an exceptional choice. The tune reached the coveted number one spot on the Billboard Hot 100, and it stayed there for a couple of weeks. The song earned the band a Grammy nomination and ultimately became platinum-certified. This meant that the song alone gained just as much notoriety as the album itself did, making it one of the biggest in the band's history.
4 Saturday In The Park
Album: Chicago V (1972)
In the early stages of their career, Chicago was off to an amazing start. By 1972, the band had already released three studio albums, with multiple hit songs emerging from them. Their fourth release, Chicago V, also featured more popular tracks. On side one, Chicago fans enjoyed the great "Dialogue (Part I)" and "Dialogue (Part II)." On side two, there was another one of their greatest hits.
For classic rock fans, the lyrics "Saturday in the park, I think, it was the fourth of July" have become iconic. They are the opening to the song "Saturday in the Park," which charted on the weekly and year-end Billboard Hot 100. While the song has been gold-certified, it is inching closer to platinum status. To this day, it remains one of the band's top songs, with millions of streams across various platforms.
3 Hard Habit To Break
Album: Chicago 17 (1984)
One of the biggest developments in the advancement of music in the '80s was the launch of MTV in August 1981. This provided musicians with a new platform to reach a larger audience. Music videos became a significant phenomenon during the decade, demonstrating that popularizing songs could be achieved in various ways. As Chicago sought to adapt to the times, they produced two of their biggest hits on their album, Chicago 17.
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The MTV Generation was exposed to countless videos on MTV, and while some may have been forgotten, there are a few that will, as they defined the era.
These two songs were "You're the Inspiration" and "Hard Habit to Break." Both songs benefited greatly from their airtime on MTV, but "Hard Habit to Break," in particular, did more. The song was nominated for four Grammy Awards and won the award for Best Arrangement, Instrumental and Vocals. A richer history of the song was established when it was covered by the underrated boy band All-4-One, which introduced it to an even wider audience.
2 If You Leave Me Now
Album: Chicago X (1976)
The 21st century has brought a variety of platforms that allow for streaming music. The numbers artists get on these have become very valuable, as they can show in real time how many people are listening to them. One of the biggest platforms is Spotify, which Chicago has done very well on, with over 10 million monthly listeners. This is an impressive number and shows how sought-after their hit songs are.
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Spotify is a great streaming platform for artists to track their music, and for some, they create a song good enough to the one billion club.
The one tune that stands above all the others is "If You Leave Me Now." In fact, it has one hundred million more streams than the next highest song, firmly securing its place as the band's greatest hit on Spotify. The song comes from their 1976 2x platinum album, Chicago X, also known as the "Chocolate Album." This record is known for its famous cover, which looks like a Hershey bar being opened to reveal Chicago's logo.
1 25 Or 6 To 4
Album: Chicago (1970)
While songs like "Does Anybody Really Know What Time It Is?," "Saturday in the Park," and "Beginnings" all come close, "25 or 6 to 4" is Chicago's most played live song with over 1,100 times counted (setlist.fm). The song comes from the band's second album, Chicago, so it has been with them since almost the beginning. From its debut, they knew it would be a key song, as it ranked as high as number four on the Billboard Hot 100.
Over the years, musicians such as Local H and Vince Neil from Mötley Crüe have covered the song. It has also become a popular tune for marching bands to perform. Additionally, it has been featured in the media for the show King of the Hill and the movie I, Tonya. As much as Chicago appreciates "25 or 6 to 4," it is clear that many others do as well. They created a hit not only for themselves, but for the rest of the world, which is no surprise, as Chicago will go down as notorious hitmakers.