The 50 Best Chicago Songs: Critics’ Picks

It’s easy to lose a band like Chicago in the towering pile of its own achievements: 36 albums, 20 Top 10 singles on the Billboard Hot 100 (including three No. 1 hits), and 17 of its first 20 albums certified Platinum by the RIAA.

But as the one of the most commercially successful American bands of all time prepares to celebrate the 50th anniversary of its debut album Chicago Transit Authority (originally released April 28, 1969), it’s time we examined the music apart from its statistical significance, and celebrated the gang of deeply gifted musicians who cemented Chicago as one of the most chameleonic acts of rock’s golden age — shifting from esoteric jazz-rock, funk and soul to an adult contemporary juggernaut.

After combing through an overwhelming amount of recorded music — four of the band’s first six LPs were double albums, mind you — here’s Billboard‘s tally of the 50 best Chicago songs. They run the gamut from deeply soulful and orchestrally tethered early contributions, courtesy of guitarist Terry Kath, keyboardist Robert Lamm, and trombonist James Pankow, to the later mega-polished super singles pumped out by bassist/singer Peter Cetera and renowned producer David Foster.

Find your favorite song (via our Spotify playlist at the bottom of the post), blast it in your earbuds and let’s all salute a band that continues to perform before thousands of fans deep into its sixth decade of rock and horns — and whose 50th birthday is still only the beginning. 

50. “I’d Rather Be Rich” (Chicago XIV, 1980)

“Everything’s cool until you lose your money,” Robert Lamm sings on this slightly jaded album track — the content of which feels prophetic considering how poorly Chicago XIV, which peaked at a paltry No. 71 on the Billboard 200 albums chart, sold in comparison to most other Chicago LPs. But this is a fun, jaunty song, with a sharp tongue and vibrant accompaniment from percussionist Laudir de Oliveira (who left the band after this album). — BOBBY OLIVIER

49. “Jenny” (from Chicago VI, 1973)

Chicago VI, the first of five straight albums to be recorded at producer James William Guerico’s Caribou Ranch in Colorado, topped the Billboard 200 due in large part to the success of singles “Just You N’ Me” and “Feelin’ Stronger Every Day.” But a more obscure fan favorite from the record is “Jenny,” a tender song written and sung by Terry Kath about Kath’s dog with the titular name. The tune, which asks Jenny to watch over and protect Kath’s lover while he’s away, is soulful and bittersweet, considering the singer-guitarist’s accidental death in 1978. — B.O.

48. “Hideaway” (from Chicago VIII, 1975)

Not a ton of Chicago riffs that you’d be likely to mistake for Tony Iommi at any point, but the chugging of Chicago VIII deep cut “Hideaway” is vicious enough that you kinda expect it to turn it into “Sabbath Bloody Sabbath” in its early minutes — even before you get to its blistering solo. The band found the majority of their success using a much lighter touch, and were wise to do so, but kudos to axeman Kath for showing when necessary that the band knows how to swing it. — ANDREW UNTERBERGER

47. “Little Miss Lovin’” (from Hot Streets, 1978)

Hot Streets was Chicago’s great sonic shift, away from the band’s defining jazz-rock mode (following the death of Kath months earlier) in favor of disco and pop. While this change in style, which would define the group’s sound throughout the ‘80s, was derided by some fans at the time, Hot Streets has aged fairly well, and the jammer “Little Miss Lovin’” is convincingly propulsive pop-rock — and if you listen closely enough, you can hear the Bee Gees singing the skyscraping background vocals. — B.O.

46. “Look Away” (from Chicago 19, 1988)

If you’re too good for Chicago’s post-Peter Cetera era, then you’re too cool for our list. There’s a whole lot of ‘80s shmaltz on Chicago 19, but this single — the band’s only No. 1 hit on the Hot 100 without Cetera, and Billboard‘s year-end No. 1 song of 1989 — remains a serious earworm, courtesy of prolific songwriter Diane Warren and Bill Champlin’s soaring lead vocals. Look away, baby, look away. — B.O.

45. “Stay The Night” (from Chicago 17, 1984)

Perhaps best-remembered for its action-packed music video, “Stay the Night” was also one of the most striking singles of Chicago’s early ’80s pop period, captivating from its opening drum hits through to its staccato verse synths and melodic left turn at the chorus. Some of the song’s more aggressive lyrics (“I won’t take no if that’s your answer”) haven’t aged particularly well, but the sneering chorus cry remains such a brain-sticker that the dudes in Foreigner are probably still seething at not having thought of it first. — A.U.

44. “Along Comes a Woman” (from Chicago 17, 1984)

Chicago’s mega-polished pop wizardry reached its zenith on Chicago 17 — the band’s best-selling record to date — as all four singles cracked the Hot 100’s top 20. The fourth and final of those was “Along Comes A Woman, a Phil Collins-esque sizzler with a hook that’s just memorable enough to make us forget about that repugnant drum machine. — B.O.

43. “Gone Long Gone” (from Hot Streets, 1978)

Here’s as good a place as any to pay homage to Donnie Dacus, the well-traveled rock guitarist who stepped in to fill the enormous hole left by Kath, and played dutifully on Hot Streets and Chicago XIII. Dacus, who also played with John Lennon, Billy Joel, and Elton John, delivers perhaps his most memorable Chicago lick on “Gone Long Gone,” a breezy tune with a Dacus’s piercing guitar melody playing foil to Cetera’s easy vocal. — B.O.

42. “Song For You” (from Chicago XIV, 1980)

Chicago XIV was the band’s lone new wave-era attempt at bucking its dance-pop approach in favor of a more introspective sound — an experiment that, of course, did not last — and Cetera’s intimate “Song For You” was this album’s great exemplifier. The singer’s more naturally produced vocal performance is nearly unrecognizable in its lower register, but still provides a soft touch, as he promises a lover he’s “a man you can be sure of.” — B.O.

41. “This Time” (from Chicago XI, 1977)

Founding trumpeter Lee Loughnane might be Chicago’s greatest unsung hero. When Loughnane wasn’t blowing his horn through all those Chicago staples, he was writing killer songs like “Call on Me,” “No Tell Lover” and this lesser-known but still very awesome track from Chicago XI, where he sings a commanding lead vocal. Kath’s guitar rips on this one, too. — B.O.

40. “Never Been In Love Before” (from Chicago VIII, 1975)

A lovely little romantic devotional from Chicago VIII, probably held back from single status by its shape-shifting nature — the song takes turns sounding like Supertramp and the Beach Boys — though it never loses its quintessential Chicago heart (or horns). Also perhaps hurting its case: Framing a song on the band’s eighth album about never having been in love before. Well then what exactly were all those other songs about, Peter?!?? — A.U.

39. “Another Rainy Day in New York City” (from Chicago X, 1976)

While Chicago X’s second single, “If You Leave Me Now,” got most of the radio play and attention as the band’s first Hot 100 No. 1 hit, “Rainy Day” was technically the record’s lead single — a light, calypso-leaning tune contrasting its dreary title. The trill-laden horn work here is strong, and the song has aged well as a fluttering warm-weather track. — B.O.

38. “Waiting for You to Decide” (from Chicago 16, 1982)

It should surprise no one that venerable producer/songwriter David Foster was in on Chicago’s shimmering ‘80s sound. He produced and co-wrote much of Chicago 16, and his melodic prowess can be felt on “Waiting For You to Decide,” a bounding album track that sets up the massive tracks “Hard to Say I’m Sorry” and “Love Me Tomorrow” later on the album. Pure ‘80s, Cetera-driven Chicago didn’t get much better than this. — B.O.

37. “State of the Union” (from Chicago V, 1972)

Perhaps it’s difficult to imagine now, but there was a time when the guys in Chicago viewed themselves as social revolutionaries, speaking out against war, politics and “the man.” “State Of The Union” is a big, feather-ruffling jam track penned by Lamm and sung by Cetera about “tearing the system down” and searching for fearless politicians to represent the common man. It an exciting song with message that is unfortunately a little too timeless. — B.O.

36. “Will You Still Love Me” (from Chicago 18, 1986)

‘It wasn’t amicable, but it wasn’t the worst,” Peter Cetera told People Magazine in 1987 about his ’85 departure from the group. “It’s nothing that me having a hit and them having a hit won’t make better.” Done and done: Following Cetera’s Karate Kid II power ballad “Glory of Love” going to No. 1 on the Hot 100, Chicago countered with their own lighter-waving “Will You Still Love Me.” The song’s brilliantly dynamic piano intro and irresistibly falsetto’d post-chorus couldn’t quite drive it to matching “Glory” on the Hot 100, but it did peak at No. 3 in early 1987, essentially tying the score between the now Jason Scheff-led group and their departed solo star. — A.U.

35. “Aire” (from Chicago VII, 1974)

Oh, to have witnessed the confused faces of those who spun Chicago VII and had to wade through a solid 25 minutes of instrumentals before the vocals to finally kicked in. The band’s final double album begins with five lushly composed pieces — the best of which is “Aire,” a sweeping number than begins with a mammoth horn solo, before taking off on Walter Parazaider’s flute and a masterful section shredded on Kath’s guitar. — B.O.

34. “Movin’ In” (from Chicago II, 1970)

At the peak of their soulful early days, Chicago kicked off their blockbuster second album with this sizzling piano groover, featuring the gritty vocals of Kath at his absolute Cockeriest. “Most of all we like to play/ A song or two that makes you feel/ Like all the good in you is real,” Kath belts, as the rest of the band chimes in “We know it!” after nearly line in ecstatic affirmation, serving as both preacher and choir to their own gospel. — A.U.

33. “Take Me Back to Chicago” (from Chicago XI, 1977)

“Take Me Back To Chicago” stands as a banner soft-rock track that bleeds with nostalgia and a dynamic performance from Lamm at the microphone. But next time you hear this third single off Chicago XI, listen closely to the backing vocal — that’s Chaka Khan! Hard not to also have a soft spot for the needling keyboard break turned in by David “Hawk” Wolinski on this one. — B.O.

32. “What’s This World Comin’ To” (from Chicago VI, 1973)

If Chicago was a hip-hop group, “What’s This World Comin’ To” would be its premier pass-the-mic banger — as Lamm, Cetera and Kath all trade lead vocals as they wonder just what the hell is going on in this crazy world full of hunger and poverty. But the coolest moment in this song, which overflows with funk and life, comes in the first few seconds, when Kath brazenly declares, “We can cut it in any key.” Chicago needed more badass moments like these. — B.O.

31. “Happy Man” (from Chicago VII, 1974)

The second-side closer to the jazzier first LP of Chicago’s 1974 double album is an unassuming sort of sun-baked ditty, gliding by on a lightly samba-ing saunter and one of Peter Cetera’s most blissed-out early vocals. Yes, Cetera can’t help himself from sticking in a little “skittle-ee-bee-bop!” scatting in there at the end, but he seems so delirious in his acting out the song’s title character that you can’t really blame him for getting caught up in the moment. — A.U.

30. “Wishing You Were Here” (from Chicago VII, 1974)

A sublime slice of gentle acoustic melancholy from its opening ocean waves, “Wishing You Were Here” proved just how evocative mid-’70s soft rock could be in the hands of the experts. Speaking of: Yep, that’s Chicago tourmates the Beach Boys joining in on backing vocals for the song’s interrupting refrain, splintering each titular lament into a veritable dirty bomb of longing in five-part harmony. — A.U.

29. “Hard Habit to Break” (from Chicago 17, 1984)

Chicago 17 is one of the greatest pure power ballad albums of all time — or at least from 1984 — and “Habit” is one of the finest entries. With a titanic melody (courtesy of songwriters Steve Kipner and Jon Parker) and monster vocals from Cetera and Champlin, this is one of those “roll the windows up and sing it as loudly and horribly as you can” Chicago tracks, and a testament to the band’s ability to thrive in its second act. — B.O.

28. “In the Country” (from Chicago II, 1970)

The magic was real on Chicago II. The level of creativity and dauntlessness in merging rock and jazz throughout this sprawling double record was just terrific, but there was a heap of soul, too, and so much of that came from Kath’s deep, impassioned wails and blistering guitar. That’s all felt in the sweeping love letter “In the Country,” where Kath sings a beautiful lead, bolstered by Cetera on backing vocal. It’s a banner conclusion to the album’s side one, setting the table for the famed “Ballet For a Girl in Buchannon” suite that soon follows. — B.O.

27. “Street Player” (from Chicago XIII, 1979)

The scorching highlight of Chicago’s short-lived disco phase, “Street Player” was written by Chicago’s Danny Seraphine and David “Hawk” Wolinski, but originally recorded by Rufus & Chaka Khan for their 1978 album of the same name. Surprisingly, it’s the Chicago rendition from a year later that’s the much funkier version, tighter and punchier and with an absolutely killer horn hook — one that improbably infiltrated two separate future generations of jock jams, via pop smashes from The Bucketheads and Pitbull. — A.U.

26. “Alive Again” (from Hot Streets, 1978)

“Alive Again” was a reintroduction of sorts for Chicago. While the band hadn’t been away all that long — Chicago XI had just come out in fall of 1977 — this was their first single released after Kath’s death, and the band’s decision to soldier on without him. “Alive Again” is a worthy, bright track written by trombonist Pankow, which showcased the band’s more pop-forward approach: It sounds like a Fleetwood Mac Rumours B-side. — B.O.

25. “Feelin’ Stronger Every Day” (from Chicago VI, 1973)

One of the most buoyant breakup songs ever written, the forever open-hearted Peter Cetera co-wrote this ’70s AM perennial with trombonist Pankow about “healing and moving on after the end of a relationship,” which with the song’s shiny horns and repeated “Oh-ohhhh yeah!” exhortations, he sounds positively friggin’ pumped about. And in case you doubt that Cetera really is getting his strength back, the song goes double-time at the end, still gaining momentum right through the fade out. On to the next one, then. — A.U.

24. “Lowdown” (from Chicago III, 1971)

The story goes that “Lowdown” was the source of some animosity within the band; Kath was apparently unhappy with yet another songwriter in Cetera, who had mostly only sang and played bass to this point, adding to the creative mix. He also wasn’t pleased with the guitar part written for “Lowdown” — but for better or worse, the bounding tune became the album’s second single and one of the most beloved tracks off Chicago III. Cetera: 1, Kath: 0. — B.O.

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 rebellious message was written on the inner cover of the Grammy-nominated Chicago II album, alongside the lyrics to “It Better End Soon,” a 10-minute long Vietnam War protest opus broken into four “movements,” all of which were sung valiantly by Kath and written by Lamm in a sort of Hendrix-meets-jazz-fusion mashup. It’s a propulsive, expansive chunk of tunage. — B.O.

22. “Dialogue, Pts. I and II” (from Chicago V, 1972)

A back-and-forth between Kath and Cetera about various early ’70s topics that probably reflected more of the push-pull tension between the two driving forces within the band than fans may have even realized at the time, “Dialogue” was released in the midst of such a commercial hot streak for Chicago that it hit the top 40 despite its lack of a chorus or obvious hook. In its full two-part, seven-minute edit, it showcases the group’s skill at displaying prog ambition within pop accessibility, nearly persuasive enough to have you believing their “We can change the world now… we can make it happen!” claims. — A.U.

21. “Beyond All Our Sorrows” (from Chicago VI reissue, 1973/2002)

“Beyond All Our Sorrows” is easily the rawest track on this entire list — it’s a gritty solo demo from Kath that didn’t appear on Chicago VI until the set’s 2002 re-release. The vocal is all soul and unbridled emotion as Kath wails over a lone piano (perhaps played himself) and reflects: “Why do I always hurt the ones I love?” If you’ve never sought out this previously unreleased tune before, loaded with power and pain, we simply urge you to do so. — B.O.

20. “Free” (from Chicago III, 1971)

Clocking in at a speedy 2:16, “Free” is the shortest track on this list, but it still packs a serious punch with Kath leading the “I just wanna be free!” chant over roaring horns and guitar. This quickie, the third of six episodes in Lamm’s “Travel Suite” on the record, was Chicago III’s lead single in 1971 and it remains a huge fan favorite nearly 50 years later. This one goes down easy, plain and simple. — B.O.

19. “No Tell Lover” (from Hot Streets, 1978)  

While the lyrical content — an ode to extramarital affairs — hasn’t particularly benefitted from the passing years, “No Tell Lover” is still a beautifully penned number from Chicago’s transition into soft-rock nobility. Cetera sings tenderly, backed by Dacus’s easy vocal and guitar. “No Tell Lover” reached No. 14 on the Hot 100 and was Chicago’s last top 50 hit for four years, until “Hard To Say I’m Sorry” came along. — B.O.

18. “Baby, What a Big Surprise” (from Chicago XI, 1977)

As we enter the “monster ballads to end all monster ballads” portion of this list, let’s talk about “Baby, What a Big Surprise,” an enduring soft-rock smash that climbed to No. 4 on the Hot 100 and notched Chicago’s final top 10 hit before Kath’s death (as well as the band’s split with longtime producer Guercio). As Cetera sings his version of “you like me, you really like me!” to an unknown lover, Beach Boys icon Carl Wilson sings the rich background vocals. Loughnane’s riveting piccolo trumpet performance is legendary here, too. — B.O.

17. “Old Days” (from Chicago VIII, 1975)

With an opening riff growling enough to presage Pink Floyd’s “In the Flesh,” the biggest Hot 100 hit off Chicago VIII quickly turns sweetly nostalgic, with bright horns, sweeping strings and lyrics yearning for “a world gone away.” That’s one of the modes that Cetera and Co. have longest excelled in, though, and the distorted guitar and groaning organ backbone to “Old Days” gives it enough muscle to keep it from ever floating away on a wistful sigh. — A.U.

16. “(I’ve Been) Searchin’ so Long” (from Chicago VII, 1974)

“Searchin’” is not only the best song off Chicago VII, it’s utter adult contemporary heaven. Cetera’s creamy vocal goes down like a vanilla milkshake, and it’s juxtaposed beautifully with the gloomy symphonic intro (penned by Pankow). The yearning is real, the harmonies are glorious and as Cetera pores over his own self discovery, the tune builds to an arresting, R&B-inspired place in the last minute or so. It’s a journey. — B.O.

15. “Make Me Smile” (from Chicago II, 1970)

For all Pankow’s songwriting efforts over the last five decades, “Ballet For a Girl in Buchannon” — the epic seven-part suite from Chicago II — is certainly among his most significant. It’s a masterstroke that leads with the buoyant track “Make Me Smile,” a booming section that was cut into a radio single and became Chicago’s first-ever Hot 100 top 10 hit. Kath unleashes a characteristically impassioned vocal here, and helped set the tone for the colossal success Chicago would enjoy throughout the ‘70s. — B.O.

14. “Poem 58” (from Chicago Transit Authority, 1969)

From the days when Chicago could be seen just as much as peers of Santana as of The Carpenters, “Poem 58” is — somewhat ironically, given its title — instrumental for most of its eight and a half minute runtime, with Kath absolutely shredding his way through the acid groove. By the time Lamm’s prose enters the equation over five minutes in, the song has transitioned from a blistering rave-up to a still-hot amble, but the focus remains on the guitars, snarling their way through a jam vicious enough to turn “If You Leave Me Now” eye-rollers into true believers. — A.U.

13. “You’re the Inspiration” (from Chicago 17, 1984)

Whether you lived through this sappy beast’s mid-’80s ubiquity or you first heard it as a kitschy cameo in the 2016 superhero movie Deadpool, there’s no denying the immensity of the chorus — which was originally written for Kenny Rogers, Cetera said in a 2004 interview. “Inspiration” climbed to No. 3 on the Hot 100 early 1985 (it was bested by “Like a Virgin” and Jack Wagner’s even cheesier “All I Need”), and was a primary reason why Chicago 17 remains the band’s best-selling album to date. — B.O.

12. “Something in This City Changes People” (from Chicago VI, 1973)

“Something in This City Changes People” might be the best non-single in Chicago’s catalog. It touts this sort of grayscale, melancholy vibe as Lamm, Kath and Loughnane sing magnificently of the ills of urban life. The descending “so sad, so sad” harmonies cut like a knife over Lamm’s warm, unforgettable piano melody. Oliveira rounds out the arrangement with tapping congas, completing a deeply underrated tune from the early chapters. — B.O.

11. “Love Me Tomorrow” (from Chicago 16, 1982)

Question: How could Chicago possibly follow up the No. 1 success of “Hard To Say I’m Sorry,” which was pretty much inescapable in 1982? Answer: With another bulletproof soft-rock jam, of course, only this time with a few more teeth. “Love Me Tomorrow” and its chest-thumping chorus were another Cetera/Foster special, full of pop life and no fat to be found. — B.O.

10. “Colour My World” (from Chicago II, 1970)

Back to “Buchannon” we go, this time hailing the suite’s fifth movement, “Colour My World,” another passage deftly sung by Kath and written by the trombonist Pankow, who used color to represent the presence of love in one’s life. Lamm’s traipsing piano part is memorable here, as is Parazaider’s searing flute solo. The story goes that Pankow conjured the arpeggiated melody while on tour and staying at a Holiday Inn — proof that you never know where rock history might strike. — B.O.

9. “If You Leave Me Now” (from Chicago X, 1976)

The easy-listening point of no return for Chicago — and perhaps not coincidentally, the first of their three Hot 100 No. 1 hits. But as far as it brought the band from their Transit Authority days, “If You Leave Me Now” remains a stunning work, particularly for its efficiency — the whole thing pivots around a french horn riff that vascillates between just two notes, and a piercing two-line refrain that serves as both verse and chorus. The pleas of the song are simple and heartfelt enough that any further elaboration would feel extraneous. And when Cetera runs out of ooh-oohs, he just sits back and let the acoustic guitars do the emoting for him. — A.U.

8. “I’m a Man” (from Chicago Transit Authority, 1969)

“I’m A Man” rumbles with more horsepower than most Chicago tunes. There’s a frenetic energy that paces this stone-cold Chicago classic (penned in part by Steve Winwood, and originally released by his Spencer Davis Group in 1967) that hits the highway with some serious shreds from Kath on guitar, and a captivating vocal tradeoff between Kath, Cetera and Lamm. While “I’m A Man” is technically a cover, it still factors in heavily with the early Chicago canon, and the extended percussion solo turned in by Seraphine gave the song new flavor when it was released on Chicago’s seminal debut. — B.O.

7. “Just You N’ Me” (from Chicago VI, 1973)

“Just You and N’ Me” is Chicago’s greatest love song, hard stop. It’s a simple, passionate composition penned by Pankow, who says he wrote this staple after an argument with his fiancee. “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” climbed to No. 4 on the Hot 100, making it the highest-charting single from the much-beloved Chicago VI album (and its sheet music was used for Pankow’s wedding announcement). — B.O.

6. “Questions 67 and 68” (from Chicago Transit Authority, 1969)

Here’s where it all began. “Questions 67 and 68” was Chicago’s very first single, a triumphant inquiry penned by Lamm as he reflected an uncertain romantic relationship he experienced in the preceding years — you guessed it — ‘67 and ‘68. The piano clangs confidently and the horns blare harmoniously here, never letting up from the moment the song kicks in. But the best parts of “Questions” just might be Cetera’s swaggy “ooh’s.” “Questions” was, of course, a harbinger of all that was to come for Chicago, but history aside, it remains a stellar jazz-rock jam. — B.O.

5. “Beginnings” (from Chicago Transit Authority, 1969)

Like an evolved “Crystal Blue Persuasion,” Chicago’s second-ever A-side (re-released more successfully two years later after missing the Hot 100 in ’69) arrives on the same bubbling bass and Sunday morning guitars as that Tommy James and the Shondells classic. But “Beginnings” is elevated by its triumphant soul vocal — arguably Lamm’s finest — along with its brilliant use of non-verbal exclamations to convey emotions too overpowering for words, and the room it gives itself to grow as its eight-minute runtime really stretches out, building to a climax of “Only the beginning!” chants that whips the band into a near-religious fervor. Any surprise that beginnings like this led to such a generally unhumble career? — A.U.

4. “Does Anybody Really Know What Time it is?” (from Chicago Transit Authority, 1969)

You’d never know it today, but when Chicago entered the studio to lay down “Does Anybody Really Know What Time It Is?” — the first song the band had ever recorded together, and an eventual classic rock staple — they really had no idea what they were doing. “We tried to record it as a band, live, all of us in the studio at once,” 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.” The guys would figure out, of course, nailing Lamm’s genre-bending anthem of late-’60s disillusionment: “We’ve all got time enough to die,” he croons, surely giving the man who had asked him for the time far more than he ever bargained for. — B.O.

3. “Saturday in the Park” (from Chicago V, 1972)

Ah, the ultimate feel-good Chicago tune and one of the band’s calling-card songs, conjured from 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 scene Lamm sets (and gleefully sings) in “Saturday” create a miniature utopia, of people laughing, dancing, a man selling ice cream. Fans latched on to the dreamscape and boosted the “real celebration” to No. 3 on the Hot 100 — Chicago’s highest-charting single to that point, as well its first single to sell 1 million copies. — B.O.

2. “Hard to Say I’m Sorry” (from Chicago 16, 1982)

With disco giving way to new wave and MTV redefining rock and pop stardom early in the decade, there was real reason to wonder if Chicago would be able to survive and thrive in the 1980s. But with a hoist from writer-producer David Foster, the band vaulted back to the top of the Hot 100 with their most undeniable ballad to date — a piano-led plea for forgiveness whose airy production couldn’t disguise the strength of the songcraft underneath, from its captivating opening line (“‘Everybody needs a little time away,’ I heard her say…”) right through its masterfully deployed climactic key change. Of course, it doesn’t work the same way without Cetera’s vocal excellence, giving his full chest to every “I WILL MAKE IT UP TO YOU!” promise — but it does still work, as evidenced by the surfeit of notable covers the song has received over the years. — A.U.

1. “25 or 6 to 4” (from Chicago II, 1970)

There’s a reason why Chicago has chosen “25 or 6 to 4” as its set closer for virtually every concert this century, including its dazzling Rock and Roll Hall of Fame induction in 2017: It’s the band’s greatest song, a banner encapsulation of the rock, soul and horns sound that has brought the sprawling outfit immeasurable success over the last 50 years. “25,” written by Lamm during a sleepless night in Los Angeles — he insists the lyrical content does not allude to drug use, despite decades of debate — was Chicago’s first Hot 100 top 5 single (No. 4) and helped introduce their jazz-infused style to the mainstream consciousness. It’s a song that has endured not only on classic-rock radio, but on high school football fields, as marching bands across the country continue to favor the towering tune. But beyond the blaring brass was an unforgettable performance from Kath, who unleashed crunching hard-rock hell on this tune, plus an urgent, high-flying vocal from Cetera. A full-band effort from one of the greatest big-band rock acts of any era. — B.O.