It’s easy to get lost in the sheer volume of Chicago’s accomplishments: a staggering 36 albums, 20 singles reaching the Top 10 on the Billboard Hot 100 chart (including three chart-toppers), and an impressive 17 of their initial 20 albums achieving Platinum certification from the RIAA. As one of the most commercially successful and enduring American rock bands of all time, Chicago’s musical catalog is ripe for deep exploration.
As we approach and celebrate the 50th anniversary of their groundbreaking debut album, Chicago Transit Authority, originally unleashed on April 28, 1969, it’s the perfect moment to delve into their music beyond the impressive statistics. Let’s celebrate the collective of exceptionally talented musicians who solidified Chicago’s status as one of rock’s most adaptable and enduring acts during its golden age. From their initial forays into complex jazz-rock fusion, funk, and soul, to their later evolution into an adult contemporary powerhouse, Chicago’s journey is a testament to musical innovation and evolution.
After meticulously sifting through their extensive discography – a task made more substantial by the fact that four of their first six LPs were ambitious double albums – Billboard presents its definitive ranking of the 50 best Chicago songs. This list traverses the spectrum of their sound, from the deeply soulful and orchestrally rich early tracks crafted by the gifted trio of guitarist Terry Kath, keyboardist Robert Lamm, and trombonist James Pankow, to the later, impeccably polished mega-hits produced by bassist/singer Peter Cetera and the renowned producer David Foster.
Discover your personal favorites (via our Spotify playlist embedded at the end of this article), immerse yourself in the music through your headphones, and join us in honoring a band that continues to captivate audiences worldwide, performing for thousands of devoted fans well into their sixth decade of making rock and roll with horns. Their 50th anniversary is not just a milestone, but a testament to a legacy that is still unfolding.
50. “I’d Rather Be Rich” (Chicago XIV, 1980)
“Everything’s cool until you lose your money,” Robert Lamm wryly observes on this often-overlooked album cut. These lyrics resonate with an almost prophetic irony, considering the commercial fate of Chicago XIV. Compared to Chicago’s usual chart dominance, the album underperformed, peaking at a modest No. 71 on the Billboard 200 albums chart. However, “I’d Rather Be Rich” itself is far from a failure. It’s a playful, jaunty track, laced with a cynical wit and enhanced by the vibrant percussion work of Laudir de Oliveira, who would depart the band after this album. This song, while not a chart-topper, offers a glimpse into a slightly more cynical, but still musically engaging, side of Chicago.
49. “Jenny” (from Chicago VI, 1973)
Chicago VI marked the beginning of a highly successful period for the band, being the first of five consecutive albums recorded at producer James William Guerico’s Caribou Ranch in Colorado. The album soared to the top of the Billboard 200, fueled by the popularity of singles like “Just You N’ Me” and “Feelin’ Stronger Every Day.” However, nestled within this hit-laden album is “Jenny,” a more understated gem beloved by dedicated fans. This tender ballad, written and sung by the late Terry Kath, is a heartfelt ode to Kath’s dog, Jenny, for whom the song is named. The lyrics poignantly ask Jenny to watch over and protect Kath’s lover during his absences. Knowing Kath’s tragic accidental death in 1978, the song takes on an even deeper, bittersweet resonance, transforming a simple pet tribute into a poignant reflection on love and vulnerability.
48. “Hideaway” (from Chicago VIII, 1975)
While Chicago is not typically associated with heavy rock riffs, the Chicago VIII deep cut “Hideaway” presents a surprisingly muscular and aggressive sound. The song’s opening chug is so potent that it evokes a Sabbath-esque vibe, almost teasing a transition into “Sabbath Bloody Sabbath.” Even before Kath unleashes a blistering guitar solo, the track showcases a heavier side of Chicago rarely heard in their mainstream hits. The band’s widespread success was largely built on their lighter, more melodic touch, a wise strategic choice. However, “Hideaway” serves as a powerful reminder that Terry Kath and Chicago possessed the chops to deliver hard-rocking intensity when they chose to, demonstrating their versatility beyond the ballads and pop hits.
47. “Little Miss Lovin’” (from Hot Streets, 1978)
Hot Streets represented a significant sonic shift for Chicago. Following the untimely death of Terry Kath just months prior, the band moved away from their signature jazz-rock style and ventured into disco and pop territories. This stylistic pivot, which would define much of their sound throughout the 1980s, initially drew criticism from some long-time fans. However, Hot Streets has aged surprisingly well, and “Little Miss Lovin'” stands out as a genuinely infectious and propulsive pop-rock track. Interestingly, if you listen closely to the soaring background vocals, you can hear the distinct harmonies of the Bee Gees, adding another layer of pop pedigree to this transitional track in Chicago’s discography.
46. “Look Away” (from Chicago 19, 1988)
Dismissing Chicago’s post-Peter Cetera era means missing out on some significant hits, including “Look Away.” While Chicago 19 leans heavily into the polished ’80s sound, this single, penned by prolific songwriter Diane Warren and featuring Bill Champlin’s powerful lead vocals, is undeniably catchy. “Look Away” holds a unique place in Chicago’s history as their only Hot 100 No. 1 hit that doesn’t feature Peter Cetera. Furthermore, it was Billboard’s year-end No. 1 song of 1989, solidifying its place as a major pop culture moment. Love it or find it schmaltzy, “Look Away” is an undeniable earworm and a testament to Chicago’s continued ability to produce chart-topping songs even after significant lineup changes.
45. “Stay The Night” (from Chicago 17, 1984)
“Stay the Night” is perhaps as well-remembered for its dynamic, action-packed music video as for its musical merits. It was a standout single from Chicago’s early ’80s pop phase, instantly captivating from its opening drum hits through to its staccato synth verses and the melodic shift in the chorus. While some of the lyrics, particularly lines like “I won’t take no if that’s your answer,” haven’t aged perfectly in terms of modern sensibilities, the sneering, insistent chorus remains incredibly memorable. The song’s energy and hook are so strong that it’s easy to imagine bands like Foreigner wishing they had come up with it first, highlighting Chicago’s knack for crafting impactful and catchy pop-rock anthems.
44. “Along Comes a Woman” (from Chicago 17, 1984)
Chicago 17 represented the pinnacle of Chicago’s polished pop wizardry. The album became their best-selling record to date, and its success was driven by an impressive string of singles. All four singles released from Chicago 17 cracked the Hot 100’s top 20, a remarkable feat. “Along Comes A Woman” was the fourth and final single from this blockbuster album. It’s a Phil Collins-esque, high-energy track with a hook that’s undeniably memorable, catchy enough to make listeners almost forgive the somewhat dated-sounding drum machine prominent in the production. This song exemplifies the commercially potent, finely crafted pop sound that defined Chicago in the mid-1980s.
43. “Gone Long Gone” (from Hot Streets, 1978)
“Gone Long Gone” provides a perfect opportunity to acknowledge Donnie Dacus, the talented rock guitarist who stepped into the incredibly large shoes left by Terry Kath. Dacus joined Chicago and played on both Hot Streets and Chicago XIII. Prior to Chicago, Dacus had an impressive resume, having played with artists like John Lennon, Billy Joel, and Elton John. On “Gone Long Gone,” Dacus delivers perhaps his most memorable guitar work with Chicago. The song is a breezy, easy-listening tune where Dacus’s sharp, piercing guitar melody acts as a compelling counterpoint to Peter Cetera’s smooth, effortless vocal delivery, showcasing a strong musical interplay between the new guitarist and the established vocalist.
42. “Song For You” (from Chicago XIV, 1980)
Chicago XIV marked a deliberate, though ultimately short-lived, attempt by the band to move away from their increasingly dance-pop oriented sound of the late 70s and early 80s. They experimented with a more introspective and new wave-influenced approach. This sonic shift was an experiment that, in retrospect, didn’t last long. “Song For You,” a deeply personal track written and sung by Peter Cetera, is a prime example of this album’s more intimate direction. Cetera’s vocal performance here is notably different, more naturally produced and less reliant on his higher register, making him almost unrecognizable at moments. Despite this shift, his voice retains a soft, reassuring quality as he promises a lover that he’s “a man you can be sure of,” creating a tender and vulnerable ballad within a transitional album.
41. “This Time” (from Chicago XI, 1977)
Founding trumpeter Lee Loughnane is arguably one of Chicago’s most underrated members. While he is renowned for his horn playing on countless Chicago classics, Loughnane was also a talented songwriter. He penned killer tracks like “Call on Me,” “No Tell Lover,” and “This Time,” a lesser-known but still exceptional song from Chicago XI. On “This Time,” Loughnane takes center stage with a commanding lead vocal performance. The song also features blistering guitar work from Terry Kath, making it a powerful showcase of the band’s instrumental and vocal talents beyond the more famous hits.
40. “Never Been In Love Before” (from Chicago VIII, 1975)
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A charming and romantic offering from Chicago VIII, “Never Been In Love Before” likely didn’t achieve single status due to its somewhat eclectic and shape-shifting nature. The song seamlessly blends elements reminiscent of Supertramp and the Beach Boys, yet it never loses its quintessential Chicago essence, complete with their signature heart and horn arrangements. Perhaps another factor working against its single potential is the somewhat ironic lyrical premise: on their eighth album, singing about “never having been in love before” raises a humorous question about the subject matter of their previous songs. Regardless, it’s a delightful track showcasing Chicago’s versatility and melodic gifts.
39. “Another Rainy Day in New York City” (from Chicago X, 1976)
While “If You Leave Me Now” from Chicago X became the band’s first Hot 100 No. 1 hit and garnered significant radio play and attention, “Another Rainy Day in New York City” was technically the album’s lead single. This lighter, calypso-influenced tune provides a sonic contrast to its somewhat dreary title. The horn arrangements, filled with intricate trills, are particularly strong and memorable. “Another Rainy Day in New York City” has aged gracefully as a breezy, warm-weather track, offering a different flavor compared to the heavier ballads and rock anthems in Chicago’s catalog.
48. “Waiting for You to Decide” (from Chicago 16, 1982)
It’s no surprise that the acclaimed producer and songwriter David Foster played a key role in shaping Chicago’s shimmering ’80s sound. He produced and co-wrote a significant portion of Chicago 16, and his melodic sensibilities are evident throughout the album, especially on “Waiting For You to Decide.” This upbeat album track effectively sets the stage for the album’s later massive hits, “Hard to Say I’m Sorry” and “Love Me Tomorrow.” “Waiting For You to Decide” is pure ’80s, Cetera-driven Chicago at its finest, embodying the polished, commercially appealing sound that defined this era for the band.
37. “State of the Union” (from Chicago V, 1972)
It might be hard to imagine now, but early in their career, Chicago saw themselves as socially conscious artists, speaking out against war, political corruption, and societal injustices. “State of the Union” is a powerful, thought-provoking track penned by Robert Lamm and sung by Peter Cetera. The lyrics express frustration with the political system, calling for change, “tearing the system down,” and seeking out honest politicians who truly represent the common person. It’s an energetic song with a message that, unfortunately, remains relevant and timeless, highlighting Chicago’s early engagement with social commentary through their music.
36. “Will You Still Love Me” (from Chicago 18, 1986)
Peter Cetera’s departure from Chicago in 1985 was not amicable, but as he humorously told People Magazine in 1987, “It’s nothing that me having a hit and them having a hit won’t make better.” And indeed, both parties found success after the split. Following Cetera’s chart-topping solo hit, “Glory of Love,” from Karate Kid II, Chicago responded with their own lighter-waving power ballad, “Will You Still Love Me.” The song features a brilliant and dynamic piano intro and an irresistible, falsetto-laden post-chorus. While it didn’t quite match the No. 1 peak of “Glory of Love” on the Hot 100, “Will You Still Love Me” reached a strong No. 3 in early 1987, essentially proving that both Cetera’s solo career and Chicago’s continued journey without him could thrive. This track marked a successful continuation for the band, now fronted by Jason Scheff.
35. “Aire” (from Chicago VII, 1974)
Listeners who first put on Chicago VII expecting a typical vocal-driven album were likely surprised to find themselves immersed in a solid 25 minutes of instrumental music before vocals finally appeared. Chicago’s final double album begins with five lushly orchestrated instrumental pieces, and “Aire” stands out as the best among them. It’s a sweeping and expansive composition that opens with a powerful horn solo before transitioning to Walter Parazaider’s flute and a masterful guitar section by Terry Kath. “Aire” exemplifies Chicago’s instrumental prowess and their willingness to explore complex musical textures beyond their vocal hits.
34. “Movin’ In” (from Chicago II, 1970)
In their early, soul-infused days, Chicago kicked off their blockbuster second album, Chicago II, with the sizzling piano-driven groove of “Movin’ In.” The song features the raw, gritty vocals of Terry Kath at his most Cocker-esque. Kath belts out lines like, “Most of all we like to play/ A song or two that makes you feel/ Like all the good in you is real,” with the rest of the band enthusiastically chiming in “We know it!” after nearly every line. This call-and-response dynamic creates a gospel-like fervor, positioning Chicago as both preacher and choir to their own musical gospel, showcasing their early energy and soulful roots.
33. “Take Me Back to Chicago” (from Chicago XI, 1977)
“Take Me Back To Chicago” is a quintessential soft-rock track that evokes nostalgia and features a dynamic vocal performance from Robert Lamm. The song was released as the third single from Chicago XI. However, a surprising and delightful element of this track is the backing vocal – provided by none other than the legendary Chaka Khan! Adding to the song’s appeal is a memorable keyboard break performed by David “Hawk” Wolinski, making “Take Me Back To Chicago” a rich and layered listening experience beyond its surface-level soft-rock charm.
32. “What’s This World Comin’ To” (from Chicago VI, 1973)
If Chicago were a hip-hop group, “What’s This World Comin’ To” would be their definitive pass-the-mic anthem. Robert Lamm, Peter Cetera, and Terry Kath all trade lead vocals on this track, collectively questioning the state of the world and addressing issues like hunger and poverty. The song is overflowing with funk and energy. However, one of the most memorable moments occurs right at the beginning, when Terry Kath boldly declares, “We can cut it in any key,” showcasing the band’s confidence and musical prowess. “What’s This World Comin’ To” is a reminder of Chicago’s ability to blend social commentary with infectious grooves and instrumental virtuosity.
31. “Happy Man” (from Chicago VII, 1974)
“Happy Man” serves as the second-side closer to the jazzier first LP of Chicago VII, released as a double album in 1974. It’s an unassuming, sun-drenched tune that glides along with a light samba rhythm and features one of Peter Cetera’s most blissfully relaxed early vocals. While Cetera can’t resist adding a bit of “skittle-ee-bee-bop!” scatting towards the end, his performance perfectly embodies the song’s title character. He sounds genuinely caught up in the moment, conveying the carefree joy of a “Happy Man,” making it a subtly charming and feel-good track.
30. “Wishing You Were Here” (from Chicago VII, 1974)
“Wishing You Were Here” opens with the gentle sound of ocean waves, immediately establishing a mood of sublime, acoustic melancholy. This track demonstrates how evocative mid-70s soft rock could be when crafted by experts like Chicago. Adding to the song’s emotional depth are backing vocals from their tourmates, The Beach Boys. They join in on the song’s recurring refrain, transforming each instance of the titular lament into a powerful expression of longing through five-part harmony. “Wishing You Were Here” is a testament to the power of collaboration and the emotional resonance of expertly crafted soft rock.
29. “Hard Habit to Break” (from Chicago 17, 1984)
Chicago 17 is arguably one of the greatest power ballad albums of the 1980s, and “Hard Habit to Break” is undoubtedly one of its standout tracks. With a monumental melody penned by songwriters Steve Kipner and Jon Parker, and powerhouse vocals from both Peter Cetera and Bill Champlin, this song is tailor-made for singing along at the top of your lungs. It perfectly exemplifies Chicago’s ability to not only survive but thrive in their second act, mastering the art of the power ballad and delivering emotionally resonant hits that resonated with a new generation of listeners.
28. “In the Country” (from Chicago II, 1970)
The magic of Chicago II was undeniable. The album showcased an extraordinary level of creativity and boldness in its fusion of rock and jazz, particularly evident in its sprawling double album format. Beyond the genre-bending experimentation, there was also a deep vein of soulfulness running through the music, largely stemming from Terry Kath’s impassioned vocals and searing guitar work. “In the Country” perfectly encapsulates this blend. Kath delivers a beautiful lead vocal, supported by Peter Cetera on backing vocals. It serves as a powerful conclusion to the album’s first side, setting the stage for the iconic “Ballet For a Girl in Buchannon” suite that follows, highlighting the album’s dynamic range and ambition.
27. “Street Player” (from Chicago XIII, 1979)
“Street Player” stands out as a scorching highlight from Chicago’s brief foray into disco. While written by Chicago’s Danny Seraphine and David “Hawk” Wolinski, it was originally recorded by Rufus & Chaka Khan for their 1978 album of the same name. Surprisingly, Chicago’s rendition, released a year later on Chicago XIII, is arguably the funkier and more impactful version. It’s tighter, punchier, and features an absolutely killer horn hook that has improbably infiltrated two separate future generations of jock jams. The horn riff was famously sampled in pop hits by The Bucketheads (“The Bomb! (These Sounds Fall Into My Mind)”) and Pitbull (“I Know You Want Me (Calle Ocho)”), demonstrating the song’s enduring groove and unexpected cross-generational appeal.
26. “Alive Again” (from Hot Streets, 1978)
“Alive Again” served as a reintroduction for Chicago. While they hadn’t been absent for long – Chicago XI was released just in the fall of 1977 – this was their first single released after the tragic death of Terry Kath and marked the band’s decision to continue without him. “Alive Again” is a strong, uplifting track written by trombonist James Pankow, showcasing the band’s shift towards a more pop-forward sound. It has a bright, Fleetwood Mac Rumours B-side feel, signaling a new chapter for Chicago while still maintaining their melodic strengths and musicality.
25. “Feelin’ Stronger Every Day” (from Chicago VI, 1973)
“Feelin’ Stronger Every Day” is one of the most upbeat and optimistic breakup songs ever written. Peter Cetera co-wrote this 70s AM radio staple with trombonist James Pankow. The lyrics are about “healing and moving on after the end of a relationship,” and the song’s shiny horns and repeated “Oh-ohhhh yeah!” exclamations perfectly convey a sense of exhilaration and renewed energy. The song’s positive message is amplified by its musical momentum, building to a double-time tempo towards the end, still gaining energy as it fades out, embodying the very feeling of growing stronger and moving forward.
24. “Lowdown” (from Chicago III, 1971)
The creation of “Lowdown” reportedly caused some friction within the band. Terry Kath was apparently displeased with Peter Cetera, who had primarily been a bassist and vocalist, stepping into songwriting. Kath was also reportedly not fond of the guitar part written for “Lowdown.” Despite these internal tensions, the catchy and energetic tune became the second single from Chicago III and one of its most beloved tracks. “Lowdown” showcases Cetera’s growing songwriting contributions and became another hit for the band, demonstrating their evolving dynamic and enduring appeal.
23. “It Better End Soon” (from Chicago II, 1970)
“With this album, we dedicate ourselves, our futures and our energies to the people of the revolution. And the revolution in all of its forms.” This powerful and politically charged message was inscribed on the inner cover of the Grammy-nominated Chicago II album, alongside the lyrics to “It Better End Soon.” This 10-minute epic is a Vietnam War protest song divided into four distinct “movements,” all sung passionately by Terry Kath and written by Robert Lamm. It’s a musical fusion of Hendrix-like guitar work and jazz-rock sensibilities, creating a propulsive and expansive piece of music that reflects the anti-war sentiment of the era and Chicago’s early socially conscious stance.
22. “Dialogue, Pts. I and II” (from Chicago V, 1972)
“Dialogue, Pts. I and II” is structured as a musical conversation between Terry Kath and Peter Cetera, exploring various topics relevant to the early 1970s. This back-and-forth may have mirrored the underlying creative tensions between these two key figures within the band, even if listeners weren’t fully aware at the time. Released during a period of immense commercial success for Chicago, “Dialogue” surprisingly reached the top 40 despite lacking a traditional chorus or an obvious hook. In its full seven-minute, two-part version, it showcases Chicago’s ability to blend progressive rock ambition with pop accessibility, almost convincing listeners of their hopeful claims, “We can change the world now… we can make it happen!”
21. “Beyond All Our Sorrows” (from Chicago VI reissue, 1973/2002)
“Beyond All Our Sorrows” is arguably the rawest and most emotionally exposed track on this entire list. It’s a gritty solo demo by Terry Kath that remained unreleased on the original Chicago VI album, finally surfacing on the set’s 2002 re-release. Kath’s vocal is intensely soulful and filled with unbridled emotion as he wails over a simple piano accompaniment (possibly played by Kath himself), reflecting on the painful question, “Why do I always hurt the ones I love?” This previously unheard track is a powerful and poignant discovery, loaded with both musical and emotional intensity, offering a deeper glimpse into Kath’s artistry and vulnerability.
20. “Free” (from Chicago III, 1971)
Clocking in at a concise 2 minutes and 16 seconds, “Free” is the shortest track on this list, yet it delivers a significant punch. Terry Kath leads the powerful “I just wanna be free!” chant over roaring horns and guitar. This quick, energetic track is the third part of Robert Lamm’s “Travel Suite” on Chicago III. It was released as the lead single from the album in 1971 and has remained a fan favorite for nearly 50 years. “Free” is a straightforward, instantly gratifying rock anthem that goes down easy, delivering its message of liberation with raw energy and musical punch.
19. “No Tell Lover” (from Hot Streets, 1978)
While the lyrical theme of “No Tell Lover” – an ode to extramarital affairs – may not resonate as well with contemporary audiences, it remains a beautifully crafted song from Chicago’s transition into soft-rock prominence. Peter Cetera delivers a tender vocal performance, backed by Donnie Dacus’s smooth vocals and guitar work. “No Tell Lover” reached No. 14 on the Hot 100 and marked Chicago’s last top 50 hit for four years, until “Hard To Say I’m Sorry” revitalized their chart success. Despite its potentially controversial lyrical content, the song’s musicality and vocal harmonies are undeniable.
18. “Baby, What a Big Surprise” (from Chicago XI, 1977)
As we enter the “monster ballads” section of this list, “Baby, What a Big Surprise” is a prime example. This enduring soft-rock smash climbed to No. 4 on the Hot 100 and became Chicago’s final top 10 hit before Terry Kath’s death and the band’s split with longtime producer James William Guercio. As Peter Cetera sings his version of “you like me, you really like me!” to an unnamed lover, Beach Boys icon Carl Wilson contributes rich background vocals. Lee Loughnane’s captivating piccolo trumpet performance is also legendary on this track. “Baby, What a Big Surprise” is a masterclass in soft-rock balladry, combining heartfelt vocals, lush harmonies, and memorable instrumental hooks.
17. “Old Days” (from Chicago VIII, 1975)
Opening with a riff that’s gritty enough to foreshadow Pink Floyd’s “In the Flesh,” “Old Days,” the biggest Hot 100 hit from Chicago VIII, quickly transitions into sweet nostalgia. It features bright horns, sweeping strings, and lyrics yearning for “a world gone away.” This nostalgic mode is one that Peter Cetera and Chicago have consistently excelled at. However, “Old Days” maintains a certain muscle thanks to its distorted guitar and groaning organ backbone, preventing it from becoming overly sentimental and giving it a distinctive edge within its wistful atmosphere.
16. “(I’ve Been) Searchin’ so Long” (from Chicago VII, 1974)
“(I’ve Been) Searchin’ So Long” is not only a standout track from Chicago VII, but it’s also a prime example of adult contemporary perfection. Peter Cetera’s smooth, creamy vocal delivery is like a vanilla milkshake, beautifully juxtaposed with the somber symphonic intro penned by James Pankow. The song’s yearning quality is palpable, the harmonies are glorious, and as Cetera delves into self-discovery, the tune builds to a captivating, R&B-inspired climax in its final minute. “(I’ve Been) Searchin’ So Long” is a musical journey that showcases Chicago’s ability to blend sophisticated arrangements with heartfelt emotion.
15. “Make Me Smile” (from Chicago II, 1970)
For all of James Pankow’s songwriting contributions over five decades, the “Ballet For a Girl in Buchannon” – the epic seven-part suite from Chicago II – is undoubtedly among his most significant achievements. It’s a musical masterstroke, beginning with the buoyant track “Make Me Smile.” This energetic section was edited into a radio single and became Chicago’s first-ever Hot 100 top 10 hit. Terry Kath delivers a characteristically impassioned vocal performance, setting the stage for the immense success Chicago would achieve throughout the 1970s. “Make Me Smile” is a dynamic and instantly recognizable track that captured the band’s early energy and helped propel them to mainstream stardom.
14. “Poem 58” (from Chicago Transit Authority, 1969)
From a time when Chicago could be seen as peers to both Santana and The Carpenters, “Poem 58” – somewhat ironically given its title – is primarily instrumental for most of its eight-and-a-half-minute duration. Terry Kath delivers an absolute shred-fest throughout the acid-infused groove. Robert Lamm’s spoken-word prose enters the equation more than five minutes in, by which point the song has transitioned from a blistering rave-up to a still-intense amble. However, the focus remains firmly on Kath’s guitars, snarling their way through a jam vicious enough to convert even “If You Leave Me Now” skeptics into true believers in Chicago’s instrumental prowess.
13. “You’re the Inspiration” (from Chicago 17, 1984)
Whether you experienced the omnipresence of “You’re the Inspiration” in the mid-80s or first encountered it as a kitschy cameo in the 2016 superhero movie Deadpool, the sheer magnitude of its chorus is undeniable. Originally written for Kenny Rogers, as Peter Cetera revealed in a 2004 interview, “You’re the Inspiration” climbed to No. 3 on the Hot 100 in early 1985. It was a key factor in Chicago 17 becoming the band’s best-selling album to date. This power ballad, despite its sappiness to some, is a testament to its enduring appeal and its impact on Chicago’s commercial success in the 80s.
12. “Something in This City Changes People” (from Chicago VI, 1973)
“Something in This City Changes People” is arguably the best non-single in Chicago’s entire catalog. It carries a grayscale, melancholic vibe as Robert Lamm, Terry Kath, and Lee Loughnane deliver magnificent vocals about the harsh realities of urban life. The descending “so sad, so sad” harmonies cut deep over Robert Lamm’s warm and unforgettable piano melody. Laudir de Oliveira’s subtle conga rhythms round out the arrangement, completing a deeply underrated tune from Chicago’s early and highly creative period.
11. “Love Me Tomorrow” (from Chicago 16, 1982)
Following the massive No. 1 success of “Hard To Say I’m Sorry” in 1982, the question was how Chicago could possibly follow up such a ubiquitous hit. The answer was “Love Me Tomorrow,” another bulletproof soft-rock anthem, this time with a bit more edge. “Love Me Tomorrow” and its chest-thumping chorus were another collaboration between Peter Cetera and David Foster. It’s a track packed with pop energy, lean, and expertly crafted, proving Chicago’s renewed ability to deliver hit after hit in the 1980s.
10. “Colour My World” (from Chicago II, 1970)
Returning to the “Ballet For a Girl in Buchannon” suite, this time highlighting its fifth movement, “Colour My World.” This beautiful passage is sung delicately by Terry Kath and written by trombonist James Pankow, who used color as a metaphor for the presence of love in one’s life. Robert Lamm’s gentle piano accompaniment is particularly memorable, as is Walter Parazaider’s soaring flute solo. The story goes that Pankow conceived the arpeggiated melody while on tour, staying at a Holiday Inn – a reminder that inspiration for rock history can strike anywhere, anytime.
9. “If You Leave Me Now” (from Chicago X, 1976)
“If You Leave Me Now” represents Chicago’s point of no return into the realm of easy listening – and perhaps not coincidentally, it became their first of three Hot 100 No. 1 hits. While it may seem a far cry from their Chicago Transit Authority days, “If You Leave Me Now” remains a stunningly effective song, particularly in its efficiency. The entire song revolves around a French horn riff that oscillates between just two notes and a piercing two-line refrain that serves as both verse and chorus. The song’s pleas are simple and heartfelt, requiring no further embellishment. When Peter Cetera’s vocal “ooh-oohs” subside, the acoustic guitars take over, continuing to emote and convey the song’s deep sentiment.
8. “I’m a Man” (from Chicago Transit Authority, 1969)
“I’m A Man” rumbles with more raw power than most Chicago tunes. There’s a frenetic energy that drives this stone-cold Chicago classic. Originally written by Steve Winwood and released by his Spencer Davis Group in 1967, Chicago’s version takes it to another level. It features serious guitar shredding from Terry Kath and a captivating vocal interplay between Kath, Peter Cetera, and Robert Lamm. While technically a cover, “I’m A Man” is deeply ingrained in the early Chicago canon. Danny Seraphine’s extended percussion solo adds a new dimension to the song when it was released on Chicago’s seminal debut, solidifying its place as a live performance staple and a showcase of the band’s instrumental prowess.
7. “Just You N’ Me” (from Chicago VI, 1973)
“Just You and N’ Me” is arguably Chicago’s greatest love song, full stop. It’s a simple yet deeply passionate composition penned by James Pankow. He recounted that he wrote this classic after an argument with his fiancée. “We had a disagreement, and rather than put my fist through the wall or get crazy or get nuclear, I went out to the piano, and this song just kind of poured out,” Pankow explained on Chicago’s website. “Just You N’ Me” climbed to No. 4 on the Hot 100, becoming the highest-charting single from the beloved Chicago VI album. Significantly, the sheet music for “Just You N’ Me” was even used for Pankow’s wedding announcement, further cementing its personal and romantic significance.
6. “Questions 67 and 68” (from Chicago Transit Authority, 1969)
This is where it all began. “Questions 67 and 68” was Chicago’s very first single, a triumphant and questioning song penned by Robert Lamm reflecting on an uncertain romantic relationship he experienced in the preceding years – 1967 and 1968. The piano chords clang confidently, and the horns blare harmoniously, maintaining intensity from the song’s outset. However, one of the most memorable elements of “Questions” are Peter Cetera’s signature swaggy “ooh’s.” “Questions 67 and 68” served as a harbinger of the immense success that awaited Chicago, and even decades later, it remains a stellar jazz-rock jam, showcasing their early innovative sound.
5. “Beginnings” (from Chicago Transit Authority, 1969)
Evoking a more evolved “Crystal Blue Persuasion,” Chicago’s second A-side single (successfully re-released two years later after initially missing the Hot 100 in ’69) shares a similar bubbling bassline and Sunday morning guitar vibe with the Tommy James and the Shondells classic. However, “Beginnings” is elevated by Robert Lamm’s triumphant and soulful vocal performance – arguably his finest – along with its brilliant use of non-verbal exclamations to convey overwhelming emotions. The song’s extended eight-minute runtime allows it to organically grow and build to a climax of “Only the beginning!” chants, whipping the band into a near-religious fervor. It’s little surprise that such a powerful “beginning” led to such an exceptionally successful and enduring career.
4. “Does Anybody Really Know What Time it is?” (from Chicago Transit Authority, 1969)
It’s surprising to learn that when Chicago entered the studio to record “Does Anybody Really Know What Time It Is?” – the first song they ever recorded together and a future classic rock staple – they were essentially figuring it out as they went along. “We tried to record it as a band, live, all of us in the studio at once,” Walter Parazaider recalled on the band’s website. “I just remember standing in the middle of that room. I didn’t want to look at anybody else for fear I’d throw them off and myself, too. That’s how crazy it got.” Despite the initial chaos, they ultimately nailed Robert Lamm’s genre-bending anthem of late-60s disillusionment. “We’ve all got time enough to die,” he croons, giving the person who simply asked for the time far more than they likely bargained for. “Does Anybody Really Know What Time It Is?” is a testament to the band’s ability to create magic even in the midst of uncertainty and experimentation.
3. “Saturday in the Park” (from Chicago V, 1972)
“Saturday in the Park” is the quintessential feel-good Chicago tune and one of the band’s signature songs. It was inspired by Robert Lamm’s interpretation of film footage he shot in Central Park years earlier. As he recalled to Billboard in 2017, “I watched the film [and] I jotted down some ideas based on what I was seeing and had experienced. And it was really kind of that peace and love thing that happened in Central Park and in many parks all over the world, perhaps on a Saturday, where people just relax and enjoy each other’s presence.” The scene Lamm paints (and joyfully sings about) in “Saturday in the Park” creates a miniature utopia filled with laughter, dancing, and a man selling ice cream. Fans embraced this dreamscape, propelling the “real celebration” to No. 3 on the Hot 100, becoming Chicago’s highest-charting single to that point and their first single to sell 1 million copies.
2. “Hard to Say I’m Sorry” (from Chicago 16, 1982)
As disco faded and new wave and MTV reshaped the music landscape in the early 1980s, there were doubts about Chicago’s ability to remain relevant. However, with the help of writer-producer David Foster, the band roared back to the top of the Hot 100 with “Hard to Say I’m Sorry,” their most undeniable ballad to date. This piano-led plea for forgiveness, with its airy production, couldn’t mask the strength of the songwriting underneath, from its captivating opening line (“‘Everybody needs a little time away,’ I heard her say…”) to its masterfully executed climactic key change. Of course, Peter Cetera’s exceptional vocal performance is crucial, pouring his heart into every “I WILL MAKE IT UP TO YOU!” promise. But the song’s inherent power is undeniable, evidenced by the numerous notable covers it has received over the years, solidifying its status as a timeless power ballad.
1. “25 or 6 to 4” (from Chicago II, 1970)
There’s a reason why Chicago has chosen “25 or 6 to 4” as their set closer for nearly every concert this century, including their triumphant Rock and Roll Hall of Fame induction in 2017: it is, quite simply, the band’s greatest song. It perfectly encapsulates the rock, soul, and horns sound that has brought Chicago immeasurable success over the past 50 years. Written by Robert Lamm during a sleepless night in Los Angeles – he insists the lyrics are not about drug use, despite decades of speculation – “25 or 6 to 4” became Chicago’s first Hot 100 top 5 single (No. 4) and was instrumental in introducing their jazz-infused rock style to the mainstream. The song has endured not only on classic rock radio but also on high school football fields, as marching bands across the country continue to favor this towering tune. Beyond the blaring brass, the song features an unforgettable performance from Terry Kath, who unleashes crunching hard rock guitar, and an urgent, soaring vocal from Peter Cetera. “25 or 6 to 4” is a full-band tour-de-force and a definitive statement from one of the greatest big-band rock acts of any era, making it the ultimate top song by Chicago.
