It’s easy to overlook the sheer magnitude of Chicago’s career. With 36 albums, an astounding 20 Top 10 singles on the Billboard Hot 100, including three chart-toppers, and 17 of their first 20 albums achieving Platinum status from the RIAA, their list of accomplishments is truly staggering.
As this commercially dominant American band approaches the 50th anniversary of their debut album, Chicago Transit Authority, originally released on April 28, 1969, it’s the perfect moment to delve into their music beyond the statistics. Let’s celebrate the exceptionally talented musicians who solidified Chicago’s position as one of rock’s most adaptable acts during its golden era. They seamlessly transitioned from experimental jazz-rock, funk, and soul to becoming an adult contemporary powerhouse.
Having sifted through their extensive discography – remember, four of their first six LPs were double albums – Billboard presents its definitive ranking of the 50 best Chicago Songs. This list spans their diverse sound, from the deeply soulful and orchestrally rich early tracks, largely shaped by the contributions of guitarist Terry Kath, keyboardist Robert Lamm, and trombonist James Pankow, to the later, impeccably polished mega-hits crafted by bassist/singer Peter Cetera and renowned producer David Foster.
Find your personal favorite Chicago song (via our Spotify playlist linked below), put on your headphones, and join us in honoring a band that continues to captivate audiences decades into their career. Their 50th anniversary is not just a milestone, but a testament to their enduring legacy.
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 track. The sentiment proved somewhat prophetic, as Chicago XIV, despite its musical merits, underperformed commercially compared to Chicago’s typical success, peaking at a modest No. 71 on the Billboard 200. However, “I’d Rather Be Rich” remains a delightful, upbeat song, characterized by its witty lyrics and vibrant percussion from Laudir de Oliveira, who would depart the band after this album. It’s a hidden gem in Chicago’s vast catalog, showcasing their ability to blend social commentary with infectious melodies. – BOBBY OLIVIER
49. “Jenny” (from Chicago VI, 1973)
Chicago VI marked the beginning of a fruitful 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 hit singles “Just You N’ Me” and “Feelin’ Stronger Every Day.” Yet, “Jenny,” a more under-the-radar track, has become a beloved fan favorite. Written and sung by Terry Kath, this tender ballad is about Kath’s dog, Jenny. The lyrics express a heartfelt plea for Jenny to watch over his lover during his absences. Knowing Kath’s tragic accidental death in 1978, the song takes on a particularly poignant and bittersweet quality. – B.O.
48. “Hideaway” (from Chicago VIII, 1975)
While Chicago isn’t generally associated with heavy riffs, “Hideaway,” a deep cut from Chicago VIII, delivers a surprising dose of hard rock energy. The song’s chugging rhythm possesses a raw intensity that hints at a heavier direction, almost evoking Black Sabbath in its opening moments. Terry Kath’s blistering guitar solo further reinforces this unexpected edge. Chicago’s mainstream success often came from their softer, more melodic side, a wise approach for broader appeal. However, “Hideaway” serves as a powerful reminder that Terry Kath and Chicago were more than capable of unleashing serious rock firepower when they chose to. – ANDREW UNTERBERGER
47. “Little Miss Lovin’” (from Hot Streets, 1978)
Hot Streets represented a significant sonic shift for Chicago. Following the untimely death of Terry Kath months prior, the band moved away from their signature jazz-rock fusion towards disco and pop influences. This stylistic change, which would define much of their sound in the 1980s, initially met with resistance from some long-time fans. However, Hot Streets has aged surprisingly well, and “Little Miss Lovin’” stands out as a genuinely catchy and energetic pop-rock tune. Intriguingly, if you listen closely to the soaring background vocals, you might recognize the harmonies of the Bee Gees, adding a touch of disco royalty to this transitional track. – B.O.
46. “Look Away” (from Chicago 19, 1988)
Dismissing Chicago’s post-Peter Cetera era means missing out on some significant hits. While Chicago 19 leans heavily into 80s balladry, “Look Away” remains undeniably infectious. This single holds the distinction of being the band’s only Hot 100 No. 1 hit without Cetera and was Billboard’s No. 1 song of 1989. Penned by the prolific songwriter Diane Warren and featuring Bill Champlin’s powerful lead vocals, “Look Away” is an 80s earworm that’s hard to shake, proving Chicago’s continued ability to craft chart-topping hits even as their lineup evolved. – B.O.
45. “Stay The Night” (from Chicago 17, 1984)
“Stay the Night” is perhaps as well-remembered for its action-packed music video as for its musical merits. This single was a standout from Chicago’s early 80s pop phase, captivating listeners from its distinctive opening drum beat to its staccato synth verses and the melodic shift in the chorus. While some of the lyrics, particularly the assertive lines like “I won’t take no if that’s your answer,” might feel somewhat dated today, the song’s catchy chorus remains incredibly memorable. Its aggressive pop-rock energy is so potent it’s conceivable that bands like Foreigner might still harbor a bit of envy for not having conceived of it first. – A.U.
44. “Along Comes a Woman” (from Chicago 17, 1984)
Chicago’s polished pop sensibilities reached their peak on Chicago 17, the band’s best-selling album to date. All four singles from this record broke into the Hot 100’s top 20. “Along Comes A Woman,” the fourth and final single, is a Phil Collins-esque track with a captivating hook that’s strong enough to make listeners almost overlook the somewhat dated drum machine sound. It’s a testament to Chicago’s ability to blend pop hooks with sophisticated arrangements, even in their more commercially oriented era. – B.O.
43. “Gone Long Gone” (from Hot Streets, 1978)
“Gone Long Gone” provides an opportune moment to acknowledge Donnie Dacus, the seasoned rock guitarist who stepped into the significant void left by Terry Kath. Dacus played admirably on both Hot Streets and Chicago XIII. His impressive resume includes collaborations with John Lennon, Billy Joel, and Elton John. On “Gone Long Gone,” Dacus delivers perhaps his most memorable guitar work with Chicago. It’s a breezy tune where his piercing guitar melody acts as a perfect counterpoint to Peter Cetera’s smooth vocals. This track highlights Dacus’s contribution to Chicago’s sound during a transitional period. – B.O.
42. “Song For You” (from Chicago XIV, 1980)
Chicago XIV represented the band’s brief foray into a more introspective sound, diverging from their dance-pop approach during the new wave era. This experiment, however, proved short-lived. “Song For You,” an intimate track penned and sung by Peter Cetera, perfectly exemplifies this album’s direction. Cetera’s vocal performance is unusually raw and natural, particularly in his lower register, offering a soft and reassuring tone as he pledges to a lover, “I’m a man you can be sure of.” It’s a tender ballad showcasing a different facet of Cetera’s vocal abilities. – B.O.
41. “This Time” (from Chicago XI, 1977)
Founding trumpeter Lee Loughnane often goes unrecognized for his significant contributions to Chicago. Beyond his signature horn playing on countless Chicago hits, Loughnane is also a talented songwriter, responsible for tracks like “Call on Me,” “No Tell Lover,” and “This Time.” The latter, from Chicago XI, is a lesser-known yet powerful track where he delivers a commanding lead vocal performance. Terry Kath’s guitar work is also particularly fiery on “This Time,” making it a standout in Chicago’s late 70s catalog. – B.O.
40. “Never Been In Love Before” (from Chicago VIII, 1975)
Chicago band 1970
This image captures the original lineup of the band Chicago in 1970, showcasing their early rock and roll era.
“Never Been In Love Before,” a charmingly romantic tune from Chicago VIII, likely didn’t achieve single status due to its somewhat eclectic nature. The song playfully shifts between sonic textures reminiscent of Supertramp and the Beach Boys, yet it never loses its core Chicago identity, complete with their signature horn arrangements. Perhaps another factor hindering its single potential was the somewhat ironic title for a song appearing on the band’s eighth album. It playfully begs the question: what were all those previous love songs about, Peter? – A.U.
39. “Another Rainy Day in New York City” (from Chicago X, 1976)
While “If You Leave Me Now,” Chicago X‘s second single, garnered significant radio airplay and attention as the band’s first Hot 100 No. 1 hit, “Another Rainy Day in New York City” was technically the album’s lead single. This lighthearted, calypso-infused tune offers a delightful contrast to its gloomy title. The intricate horn arrangements are a highlight, and the song has aged gracefully as a breezy, warm-weather favorite. It demonstrates Chicago’s versatility in incorporating diverse musical styles into their sound. – B.O.
38. “Waiting for You to Decide” (from Chicago 16, 1982)
It’s no surprise that the esteemed producer and songwriter David Foster played a key role in shaping Chicago’s shimmering 80s sound. He produced and co-wrote much of Chicago 16, and his melodic prowess is evident on “Waiting For You to Decide.” This upbeat album track effectively sets the stage for the massive hits “Hard to Say I’m Sorry” and “Love Me Tomorrow” that follow later on the album. “Waiting for You to Decide” exemplifies pure 80s, Cetera-era Chicago at its finest. – B.O.
37. “State of the Union” (from Chicago V, 1972)
It might be hard to imagine now, but Chicago once saw themselves as social commentators, speaking out against war, political corruption, and societal issues. “State of the Union” is a powerful, thought-provoking track penned by Lamm and sung by Cetera. It’s a call to action about “tearing the system down” and seeking out honest politicians to represent the common person. The song’s energetic musicality and unfortunately timeless message about social and political disillusionment make it a compelling listen even today. – B.O.
36. “Will You Still Love Me” (from Chicago 18, 1986)
“It wasn’t amicable, but it wasn’t the worst,” Peter Cetera remarked to People Magazine in 1987 regarding his 1985 departure from Chicago. “It’s nothing that me having a hit and them having a hit won’t make better.” Indeed, both sides achieved subsequent success. Following Cetera’s chart-topping Karate Kid II ballad “Glory of Love,” Chicago responded with their own lighter-waving anthem, “Will You Still Love Me.” The song’s dynamic piano intro and irresistible falsetto post-chorus propelled it to No. 3 on the Hot 100 in early 1987, essentially marking a musical and commercial parity between the Jason Scheff-led Chicago and their former frontman. – A.U.
35. “Aire” (from Chicago VII, 1974)
Listeners who put on Chicago VII for the first time might have been surprised to find themselves immersed in 25 minutes of instrumental music before vocals finally appeared. This double album begins with five richly orchestrated instrumental pieces, with “Aire” being a standout. It’s a sweeping composition that commences with a grand horn solo, then transitions to Walter Parazaider’s flute and a masterful guitar section by Terry Kath. “Aire” showcases Chicago’s instrumental prowess and their willingness to explore extended musical forms. – B.O.
34. “Movin’ In” (from Chicago II, 1970)
During their early, soul-infused period, Chicago launched their blockbuster second album with “Movin’ In,” a sizzling, piano-driven track featuring Terry Kath’s raw, Cocker-esque vocals. Kath belts out, “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 echoing “We know it!” after nearly every line, acting as both preacher and choir to their own musical gospel. “Movin’ In” encapsulates the band’s early energy and soulful performance style. – A.U.
33. “Take Me Back to Chicago” (from Chicago XI, 1977)
“Take Me Back To Chicago” is a quintessential soft-rock track brimming with nostalgia, highlighted by Robert Lamm’s emotive vocals. Next time you hear this third single from Chicago XI, pay close attention to the backing vocals – it’s Chaka Khan! The song also features a memorable keyboard break by David “Hawk” Wolinski, adding another layer of musicality to this sentimental favorite. It’s a testament to Chicago’s ability to blend heartfelt lyrics with sophisticated musical arrangements. – B.O.
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 ultimate pass-the-mic anthem. Robert Lamm, Peter Cetera, and Terry Kath share lead vocals, collectively pondering the state of a world plagued by hunger and poverty. However, the most striking moment of this funky and vibrant song occurs in the opening seconds, when Kath boldly declares, “We can cut it in any key.” Chicago could have benefited from incorporating more of this kind of confident, assertive energy into their music. – B.O.
31. “Happy Man” (from Chicago VII, 1974)
“Happy Man,” the closing track on the jazzier first LP of Chicago’s 1974 double album, is a subtly captivating, sun-drenched tune. It glides along with a light samba rhythm and features one of Peter Cetera’s most blissfully relaxed early vocal performances. While Cetera can’t resist adding a bit of “skittle-ee-bee-bop!” scatting at the end, his portrayal of the song’s title character is so convincingly joyful that it’s easy to forgive his spontaneous vocal flourishes. It’s a laid-back and charming example of Chicago’s softer side. – A.U.
30. “Wishing You Were Here” (from Chicago VII, 1974)
“Wishing You Were Here” is a sublime example of gentle acoustic melancholy, beginning with the evocative sound of ocean waves. This track demonstrates the emotional depth that mid-70s soft rock could achieve in the hands of master musicians. Adding to the song’s appeal, Chicago’s tour partners, The Beach Boys, contribute backing vocals to the recurring refrain, transforming each expression of longing into a powerful five-part harmony. It’s a poignant and beautifully crafted ballad. – A.U.
29. “Hard Habit to Break” (from Chicago 17, 1984)
Chicago 17 stands as one of the quintessential power ballad albums of the 1980s, and “Hard Habit to Break” is a prime example of its excellence. With a monumental melody crafted by songwriters Steve Kipner and Jon Parker, and powerful vocals from Peter Cetera and Bill Champlin, this is a quintessential “roll down the windows and sing along” Chicago track. It’s a testament to the band’s ability to not only survive but thrive in their second act, embracing the power ballad era with remarkable success. – B.O.
28. “In the Country” (from Chicago II, 1970)
The creative energy on Chicago II was palpable. The album’s bold fusion of rock and jazz was truly remarkable, but it also possessed a deep vein of soul, largely stemming from Terry Kath’s passionate vocals and searing guitar work. “In the Country,” a sweeping love letter, perfectly encapsulates this blend. Kath delivers a beautiful lead vocal, supported by Peter Cetera’s backing harmonies. It serves as a fitting conclusion to the album’s first side, setting the stage for the renowned “Ballet For a Girl in Buchannon” suite that follows. – B.O.
27. “Street Player” (from Chicago XIII, 1979)
“Street Player” shines as a highlight of Chicago’s brief disco period. 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, is the funkier version, tighter, punchier, and boasting an absolutely killer horn hook. This iconic hook has improbably permeated two subsequent generations of jock jams, sampled in pop hits by The Bucketheads and Pitbull. – A.U.
26. “Alive Again” (from Hot Streets, 1978)
“Alive Again” served as a reintroduction for Chicago. While the band hadn’t been absent long – Chicago XI was released in the fall of 1977 – this was their first single after Terry Kath’s tragic passing, signaling their decision to continue without him. “Alive Again” is a strong, optimistic track penned by trombonist James Pankow, showcasing the band’s move towards a more pop-oriented sound. It possesses a bright, Fleetwood Mac Rumours B-side vibe, indicating a fresh direction for Chicago. – B.O.
25. “Feelin’ Stronger Every Day” (from Chicago VI, 1973)
“Feelin’ Stronger Every Day” is one of the most uplifting breakup songs ever created. Co-written by the eternally optimistic Peter Cetera and trombonist James Pankow, the song is about “healing and moving on after the end of a relationship.” With its vibrant horns and repeated “Oh-ohhhh yeah!” exclamations, Cetera sounds genuinely thrilled about moving forward. To underscore this feeling of empowerment, the song accelerates into double-time towards the end, gaining momentum right through the fade-out, perfectly embodying the sentiment of moving on to new beginnings. – A.U.
24. “Lowdown” (from Chicago III, 1971)
The creation of “Lowdown” reportedly caused some friction within the band. Terry Kath was allegedly displeased with Peter Cetera, primarily known as bassist and vocalist, becoming another songwriter in the group. He was also reportedly critical of the guitar part written for “Lowdown.” Regardless of internal tensions, the catchy tune became the album’s second single and a fan favorite from Chicago III. It marked a songwriting success for Cetera and further cemented Chicago’s diverse musical approach. – B.O.
23. “It Better End Soon” (from Chicago II, 1970)
This photograph captures the band Chicago at their Rock and Roll Hall of Fame induction in 2017, celebrating their enduring musical legacy.
“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 message was inscribed on the inner sleeve of the Grammy-nominated Chicago II album, alongside the lyrics to “It Better End Soon.” This 10-minute Vietnam War protest epic is divided into four “movements,” all sung passionately by Terry Kath and written by Robert Lamm. It’s a musical fusion of Hendrix-esque guitar work and jazz influences, resulting in a dynamic and expansive piece of music. – B.O.
22. “Dialogue, Pts. I and II” (from Chicago V, 1972)
“Dialogue, Pts. I and II” is a musical conversation between Terry Kath and Peter Cetera, addressing various topical issues of the early 70s. This back-and-forth likely mirrored the creative dynamics and occasional tensions between these two driving forces within Chicago, although fans might not have fully recognized it at the time. Despite lacking a conventional chorus or obvious hook, “Dialogue” reached the top 40, propelled by Chicago’s incredible commercial momentum at the time. In its full seven-minute, two-part version, the song highlights Chicago’s ability to blend progressive ambition with pop accessibility, almost convincing listeners of their idealistic claim, “We can change the world now… we can make it happen!” – A.U.
21. “Beyond All Our Sorrows” (from Chicago VI reissue, 1973/2002)
“Beyond All Our Sorrows” is arguably the most raw and emotionally direct track on this entire list. This gritty solo demo from Terry Kath wasn’t included on the original Chicago VI album and only surfaced on the 2002 re-release. Kath’s vocal performance is full of soul and unbridled emotion as he wails over a simple piano accompaniment (possibly played by Kath himself), reflecting on the poignant question, “Why do I always hurt the ones I love?” If you haven’t yet discovered this previously unreleased gem, brimming with power and vulnerability, it’s highly recommended listening for any Chicago fan seeking a deeper understanding of Kath’s artistry. – B.O.
20. “Free” (from Chicago III, 1971)
Clocking in at a concise 2:16, “Free” is the shortest song on this list, yet it packs a considerable punch. Terry Kath leads a powerful “I just wanna be free!” chant over roaring horns and guitar riffs. This brief track, the third of six parts in Robert Lamm’s “Travel Suite” on Chicago III, was the album’s lead single in 1971 and remains a fan favorite nearly half a century later. “Free” is a straightforward, high-energy rock anthem that resonates with its simple yet universal message of liberation. – B.O.
19. “No Tell Lover” (from Hot Streets, 1978)
While the lyrical theme of “No Tell Lover” – an ode to extramarital affairs – may not have aged perfectly in terms of social mores, it remains a beautifully crafted song from Chicago’s transition into soft-rock prominence. Peter Cetera delivers a tender vocal performance, supported by Donnie Dacus’s smooth harmonies 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 the arrival of “Hard To Say I’m Sorry.” It represents a key turning point in their sound and commercial trajectory. – B.O.
18. “Baby, What a Big Surprise” (from Chicago XI, 1977)
Entering the “monster ballad” section of this list, “Baby, What a Big Surprise” is an enduring soft-rock smash that climbed to No. 4 on the Hot 100. It also 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 a defining element of this classic ballad. – B.O.
17. “Old Days” (from Chicago VIII, 1975)
With an opening riff reminiscent of 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 sentimental mode is a strength of Cetera and Chicago, and the song’s distorted guitar and groaning organ provide enough grit to prevent it from becoming overly saccharine. “Old Days” balances wistful reflection with a touch of rock edge. – A.U.
16. “(I’ve Been) Searchin’ so Long” (from Chicago VII, 1974)
“Searchin’” is not only a standout track from Chicago VII, but it’s also a prime example of adult contemporary perfection. Peter Cetera’s smooth vocal delivery is as comforting as a vanilla milkshake, beautifully juxtaposed with the somber symphonic intro penned by James Pankow. The sense of yearning is palpable, the harmonies are glorious, and as Cetera explores themes of self-discovery, the song builds to a captivating, R&B-infused climax in its final minute. “(I’ve Been) Searchin’ so Long” is a musical journey that rewards repeated listens. – B.O.
15. “Make Me Smile” (from Chicago II, 1970)
James Pankow’s songwriting contributions are vast and significant over Chicago’s five decades, and “Ballet For a Girl in Buchannon” – the epic seven-part suite from Chicago II – is undoubtedly among his most important works. This masterpiece begins with the buoyant “Make Me Smile,” a powerful section that was edited into a radio single and became Chicago’s first-ever Hot 100 top 10 hit. Terry Kath delivers a characteristically passionate vocal performance, setting the stage for Chicago’s immense success throughout the 1970s. – B.O.
14. “Poem 58” (from Chicago Transit Authority, 1969)
From a time when Chicago could be viewed as peers of both Santana and The Carpenters, “Poem 58” is, somewhat ironically given its title, primarily instrumental for most of its eight-and-a-half-minute duration. Terry Kath’s guitar work is absolutely blistering throughout this acid-rock groove. When Robert Lamm’s spoken-word poetry enters after five minutes, the song transitions from a frenetic rave-up to a still-intense amble. However, the focus remains on Kath’s guitars, which snarl through a jam powerful enough to convert even “If You Leave Me Now” skeptics into true Chicago believers. – A.U.
13. “You’re the Inspiration” (from Chicago 17, 1984)
Whether you experienced the ubiquity of this sentimental ballad in the mid-80s or first encountered it as a kitschy cameo in the 2016 film Deadpool, the sheer magnitude of its chorus is undeniable. Originally written for Kenny Rogers, as Peter Cetera mentioned in a 2004 interview, “Inspiration” climbed to No. 3 on the Hot 100 in early 1985. It was a key factor in making Chicago 17 the band’s best-selling album to date, solidifying their power ballad dominance. – B.O.
12. “Something in This City Changes People” (from Chicago VI, 1973)
“Something in This City Changes People” might be the most exceptional non-single in Chicago’s entire catalog. It carries a grayscale, melancholy vibe as Robert Lamm, Terry Kath, and Lee Loughnane deliver magnificent vocal performances about the harsh realities of urban life. The descending “so sad, so sad” harmonies cut deeply over Lamm’s warm, unforgettable piano melody. Laudir de Oliveira’s subtle conga rhythms complete the arrangement, making this an deeply underrated song from Chicago’s early years. – B.O.
11. “Love Me Tomorrow” (from Chicago 16, 1982)
How could Chicago possibly follow up the monumental success of “Hard To Say I’m Sorry,” which was virtually inescapable in 1982? The answer: with another bulletproof soft-rock anthem, this time with a bit more edge. “Love Me Tomorrow” and its chest-thumping chorus were another Peter Cetera/David Foster collaboration, packed with pop energy and devoid of any filler. It showcased Chicago’s ability to consistently deliver high-quality, commercially successful soft rock in the 80s. – B.O.
10. “Colour My World” (from Chicago II, 1970)
Returning to “Buchannon,” we highlight the suite’s fifth movement, “Colour My World.” Another passage beautifully sung by Terry Kath and written by James Pankow, the song uses color as a metaphor for the presence of love in life. Robert Lamm’s graceful piano part and Walter Parazaider’s soaring flute solo are memorable highlights. The story goes that Pankow conceived the arpeggiated melody while on tour at a Holiday Inn, proving that inspiration for rock history can strike anywhere. – B.O.
9. “If You Leave Me Now” (from Chicago X, 1976)
“If You Leave Me Now” marked Chicago’s definitive move into easy listening territory – and perhaps not coincidentally, became their first of three Hot 100 No. 1 hits. Despite its stylistic departure from their Transit Authority days, it remains a stunningly effective song, particularly in its simplicity. The entire track revolves around a French horn riff that oscillates between just two notes and a poignant two-line refrain that functions as both verse and chorus. The song’s heartfelt pleas are so direct and sincere that any further elaboration would feel superfluous. When Peter Cetera’s ooh-oohs subside, the acoustic guitars take over, expressing the remaining emotion. – A.U.
8. “I’m a Man” (from Chicago Transit Authority, 1969)
“I’m A Man” possesses more raw power than most Chicago songs. There’s a frenetic energy driving this stone-cold Chicago classic (co-written by Steve Winwood and originally released by his Spencer Davis Group in 1967). It explodes with Terry Kath’s searing guitar riffs and a captivating vocal exchange between Kath, Peter Cetera, and Robert Lamm. While technically a cover, “I’m A Man” is deeply embedded in Chicago’s early canon. Danny Seraphine’s extended percussion solo added a fresh dimension when it was included on Chicago’s seminal debut album, showcasing their instrumental virtuosity. – B.O.
7. “Just You N’ Me” (from Chicago VI, 1973)
“Just You and N’ Me” is arguably Chicago’s greatest love song. This simple yet deeply passionate composition was penned by James Pankow, who revealed he wrote it 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 recounted on Chicago’s website. “Just You N’ Me” reached No. 4 on the Hot 100 and became the highest-charting single from the beloved Chicago VI album, and its sheet music was even used for Pankow’s wedding announcement, cementing its personal significance. – B.O.
6. “Questions 67 and 68” (from Chicago Transit Authority, 1969)
“Questions 67 and 68” is where it all began. Chicago’s very first single, this triumphant song was written by Robert Lamm reflecting on an uncertain romantic relationship he experienced in – you guessed it – 1967 and 1968. The piano chords clang confidently, and the horns blare harmoniously from the outset. Peter Cetera’s signature “ooh’s” are a standout element. “Questions 67 and 68” foreshadowed Chicago’s future success and, beyond its historical significance, remains a stellar jazz-rock composition. – B.O.
5. “Beginnings” (from Chicago Transit Authority, 1969)
Resembling an evolved “Crystal Blue Persuasion,” Chicago’s second A-side (re-released with greater success two years after initially missing the Hot 100 in 1969) shares a similar bubbling bassline and gentle, Sunday morning guitar feel as the Tommy James and the Shondells classic. However, “Beginnings” is elevated by Robert Lamm’s soulful and triumphant 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 gradually build, culminating in a crescendo of “Only the beginning!” chants, driving the band into a near-spiritual fervor. It’s hardly surprising that such beginnings led to such an extraordinary career. – A.U.
4. “Does Anybody Really Know What Time it is?” (from Chicago Transit Authority, 1969)
It might be 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 unsure of their direction. “We tried to record it as a band, live, all of us in the studio at once,” Walter Parazaider recalls 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 initial uncertainty, they ultimately nailed Robert Lamm’s genre-bending anthem of late-60s disillusionment: “We’ve all got time enough to die,” he sings, offering a far deeper answer to the time-related question than initially anticipated. – B.O.
3. “Saturday in the Park” (from Chicago V, 1972)
“Saturday in the Park” is the quintessential feel-good Chicago song and one of their signature tracks, inspired by Robert Lamm’s interpretation of film footage he’d 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 idyllic scene Lamm paints in “Saturday” – people laughing, dancing, an ice cream vendor – creates a miniature utopia. Fans embraced this dreamscape, propelling the “real celebration” to No. 3 on the Hot 100 and making it Chicago’s highest-charting single to that point, as well as their first million-selling single. – B.O.
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 80s, Chicago’s ability to remain relevant was uncertain. However, with the help of writer-producer David Foster, the band soared back to the top of the Hot 100 with their most undeniable ballad to date. “Hard to Say I’m Sorry” is a piano-driven plea for forgiveness whose polished production couldn’t conceal the underlying songwriting strength. From its captivating opening line (“‘Everybody needs a little time away,’ I heard her say…”) to its masterfully executed key change, the song is a masterclass in ballad construction. Of course, Peter Cetera’s exceptional vocal performance, fully committing to every “I WILL MAKE IT UP TO YOU!” promise, is indispensable. The song’s enduring appeal is evident in the numerous notable covers the song has received over the years, solidifying its status as a timeless classic. – A.U.
1. “25 or 6 to 4” (from Chicago II, 1970)
There’s a reason 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’s their greatest song. It perfectly encapsulates the rock, soul, and horn-driven sound that has brought the sprawling band immense success over the past 50 years. Written by Robert Lamm during a sleepless night in Los Angeles – he maintains 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). It helped introduce their jazz-infused style to the mainstream. The song has endured not only on classic rock radio but also on high school football fields, favored by marching bands nationwide. Beyond the powerful brass arrangement, the song features an unforgettable performance from Terry Kath, unleashing hard-rock intensity, and Peter Cetera’s urgent, soaring vocals. “25 or 6 to 4” is a full-band tour-de-force from one of the greatest big-band rock acts of any era, and the ultimate Chicago song. – B.O.
