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Top 15 Chicago Songs of All Time

by YPB Team

Horn-driven anthems, tender ballads and chart-topping comebacks span a band that reinvented itself across generations. Which song wins your vote?

  1. Colour My World — ranked #11
    Colour My World
    The tender 1970 ballad that became a wedding and prom staple.
    1000pts
  2. 25 or 6 to 4 — ranked #22
    25 or 6 to 4
    The 1970 brass-rock anthem built around its iconic descending guitar riff.
    943pts
  3. Hard Habit to Break — ranked #33
    Hard Habit to Break
    The 1984 Grammy-nominated ballad about lost love.
    800pts
  4. If You Leave Me Now — ranked #44
    If You Leave Me Now
    The band's 1976 number-one ballad that won a Grammy for Record of the Year.
    771pts
  5. Just You 'n' Me — ranked #55
    Just You 'n' Me
    The romantic 1973 top-five hit driven by its memorable sax solo.
    692pts
  6. Does Anybody Really Know What Time It Is? — ranked #66
    Does Anybody Really Know What Time It Is?
    The reflective 1970 hit opening with its famous flugelhorn intro.
    600pts
  7. Saturday in the Park — ranked #77
    Saturday in the Park
    The sunny 1972 single inspired by a July 4th in New York's Central Park.
    600pts
  8. You're the Inspiration — ranked #88
    You're the Inspiration
    The 1984 Peter Cetera-led power ballad and adult-contemporary smash.
    600pts
  9. Old Days — ranked #99
    Old Days
    The nostalgic 1975 single celebrating childhood memories.
    600pts
  10. Make Me Smile — ranked #1010
    Make Me Smile
    The 1970 horn-fueled hit excerpted from the Ballet for a Girl in Buchannon suite.
    491pts
  11. Feelin' Stronger Every Day — ranked #1111
    Feelin' Stronger Every Day
    The uplifting 1973 single co-written by Peter Cetera and James Pankow.
    360pts
  12. Hard to Say I'm Sorry — ranked #1212
    Hard to Say I'm Sorry
    The 1982 comeback ballad that returned Chicago to the top of the charts.
    360pts
  13. Wishing You Were Here — ranked #1313
    Wishing You Were Here
    The wistful 1974 hit featuring backing vocals from the Beach Boys.
    0pts
  14. Beginnings — ranked #1414
    Beginnings
    The exuberant 1971 single showcasing the band's signature horn section.
    0pts
  15. Look Away — ranked #1515
    Look Away
    The band's 1988 number-one breakup ballad and Billboard year-end topper.
    0pts

#Music839#Rock211#70s104#Chicago1

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