Compiling a list of Top 10 Chicago Songs brought us back to the band's endlessly inventive beginnings in 1967. Then called the Chicago Transit Authority, they'd eventually take the merging of jazz and rock to new heights.

The idea of horns in rock 'n' roll was nothing new. (Ask fellow Chicago natives the Buckinghams.) Still, the idea of a fully functioning rock and roll band that included a horn section was. New Yorkers Blood, Sweat & Tears and Canadian band Lighthouse were stomping similar ground, but it would be Chicago who took the sound to the masses.

Though their debut album, released in the spring of 1969, was full of great songs, the singles failed to catch. It would be the band's second release, simply titled Chicago, that would make the public take notice. That album spawned three Top 10 hits.

Chicago's fortunes kept rising throughout the '70s though, by the following decade, they had become a faint vision of their former selves artistically. Fans of pop hits like "If You Leave Me Now" and "Hard Habit to Break" might just fall over dead upon hearing such early things as "A Hit by Varese" or "Free Form Guitar," which is literally seven minutes of feedback from guitarist Terry Kath.

Despite several personnel changes over the years, Chicago has never stopped, and their fan base remains among the most loyal of all. With 15 Top 20 albums (including 5 that reached No. 1) and 21 Top 10 singles, Chicago has remained a consistent concert attraction and a mainstay on classic rock radio. But which songs were the best of the best? Here's our take on the Top 10 Chicago Songs.

  • 10


    From "Chicago III" (1970)

    "Free" was a top 20 hit for the band in early 1971. Taken from Chicago's third album, it shows off a funkier side of the fearless rockers. With horns to the front, it is perhaps one of the best examples of "jazz rock." (Not "fusion," mind you; that is a different and often ugly beast.) "Free" keeps the dynamics of a big band with the electric energy of rock and roll.

  • 9

    "Questions 67 and 68"

    From: "Chicago Transit Authority" (1969)

    Released in the summer of 1969, "Questions 67 And 68" was Chicago's debut single. Coming just a few months after the LP's release, it was met with silence at radio and retail. Yet composer and keyboardist Robert Lamm, who shares the vocal duties with bassist Peter Cetera, provides a clear early example of the signature Chicago sound.

  • 8

    "Feelin' Stronger Every Day"

    From: "Chicago VI" (1973)

    Written by bassist Peter Cetera and horn player James Pankow, "Feelin' Stronger Every Day" captures Chicago at the tail end of their original model. It still captures the emotion and energy of the band's early work, while pointing to a more pop-centered future. Another Top 10 hit for Chicago, it's still pretty hard to resist this track's triumphant kick of energy. Also, this seems like a good time to point out the brilliant drumming of Danny Seraphine, a vastly underrated powerhouse behind the kit.

  • 7

    "A Hit by Varese"

    From: "Chicago V" (1972)

    Chicago were nothing if not daring. Consider this: Their first three albums were all double LPs. For the fourth, a live album, Chicago stretched it to four albums. So, for album No. 5, they did the outlandish thing of releasing a single LP! Issued in 1972, Chicago V was a condensing of ideas into a simpler form. The album ran the gamut from the pure pop of "Saturday in the Park," to this LP opener which is the essence of jazz rock and finds Chicago as forward thinking as ever. The title is a reference to experimental classical composer Edgar Varese, an early innovator in electronic music, among other things.

  • 6

    "Saturday in the Park"

    From: "Chicago V" (1972)

    In the summer of 1972, you couldn't escape the sounds of "Saturday in the Park." It was everywhere. Chicago took the lessons learned from their previous hits and condensed the essence of those songs into a pure and joyous four-minute pop record. At No. 3, it quickly became their biggest hit to date, and helped make Chicago V the band's first chart-topping LP.

  • 5

    "Does Anybody Really Know What Time It Is?"

    From: "Chicago Transit Authority" (1969)

    One of the many standout tracks on Chicago's debut, "Does Anybody Really Know What Time It Is?" found fortune a year later when it was finally released as a single. Following the huge success of the three singles from Chicago's second album in 1970, Columbia Records went back and issued this as a single in late 1970. It hit the Top 10 before year's end, and is still a beloved mainstay of Chicago's playlist.

  • 4

    "Dialogue Parts 1 & 2"

    From: "Chicago V" (1972)

    One of the more interesting tracks on the band's fifth album, this plays out like an actual conversation between Peter Cetera and Terry Kath as they exchange lines on the lead vocal. Each occupies a different thought and space within the lyric. The original seven minute-plus album track was edited down for a single, which failed to replicate the smash of "Saturday in the Park," just missing the Top 20. In both its world-changing message and gospel-tinged refrain, this song is very much of its time. But there's nothing wrong with that; we can always use a little idealism.

  • 3

    "Make Me Smile"

    From: "Chicago" (1970)

    Originally "Make Me Smile" was simply one section in the complex, multi-part suite called "Ballet for a Girl in Buchannon" which took up all of side two of Chicago's second album. Someone knew a hit when they heard it, however, and the "Make Me Smile" section was extracted and edited into one concise and joyous single. Sung by guitarist Terry Kath, it became Chicago's first big hit, clocking in at No. 9 in the summer of 1970.

  • 2


    From: "Chicago Transist Authority" (1969)

    Originally found as the closing track on side one of their debut LP, "Beginnings" was an eight-minute tour de force. Edited down and released as the second single from the album, however, this Robert Lamm song failed to even chart – at least, at first. Re-released two years later, "Beginnings" hit No. 7. That version certainly is immediate; still, the more satisfying album version shows Chicago stretching out and doing what they did best.

  • 1

    "25 or 6 to 4"

    From: "Chicago" (1970)

    Though they were perhaps best known for that horn section (and, alas, in later years would turn to bland balladry), what many tend to forget is Chicago was one hell of a rock and roll band. The key to that fire was, in large part, the massive talent of guitarist Terry Kath. We will go out on a limb here and say that Kath remains one of the most underrated and unsung guitar heroes ever. "25 Or 6 To 4" hit No. 4 on the charts and was often the centerpiece of the band's live shows, as Kath would venture off into the stratosphere. One of the greatest guitar riffs of all time drives this tune from start to finish. Any non believers only need to check out this live version from 1970. You can thank us later.

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