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)