# Top 15 Chicago Songs of All Time

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

*By YPB Team · Published June 23, 2026 · https://youpick.best/ranking/top-15-chicago-songs-of-all-time*

---

## Current results (3 votes)

1. **Colour My World** — 33.33% (1 votes · score 1000/1000)
   The tender 1970 ballad that became a wedding and prom staple.
2. **25 or 6 to 4** — 33.33% (1 votes · score 943/1000)
   The 1970 brass-rock anthem built around its iconic descending guitar riff.
3. **Hard Habit to Break** — 33.33% (1 votes · score 800/1000)
   The 1984 Grammy-nominated ballad about lost love.
4. **If You Leave Me Now** — 0% (0 votes · score 771/1000)
   The band's 1976 number-one ballad that won a Grammy for Record of the Year.
5. **Just You 'n' Me** — 0% (0 votes · score 692/1000)
   The romantic 1973 top-five hit driven by its memorable sax solo.
6. **Does Anybody Really Know What Time It Is?** — 0% (0 votes · score 600/1000)
   The reflective 1970 hit opening with its famous flugelhorn intro.
7. **Saturday in the Park** — 0% (0 votes · score 600/1000)
   The sunny 1972 single inspired by a July 4th in New York's Central Park.
8. **You're the Inspiration** — 0% (0 votes · score 600/1000)
   The 1984 Peter Cetera-led power ballad and adult-contemporary smash.
9. **Old Days** — 0% (0 votes · score 600/1000)
   The nostalgic 1975 single celebrating childhood memories.
10. **Make Me Smile** — 0% (0 votes · score 491/1000)
   The 1970 horn-fueled hit excerpted from the Ballet for a Girl in Buchannon suite.
11. **Feelin' Stronger Every Day** — 0% (0 votes · score 360/1000)
   The uplifting 1973 single co-written by Peter Cetera and James Pankow.
12. **Hard to Say I'm Sorry** — 0% (0 votes · score 360/1000)
   The 1982 comeback ballad that returned Chicago to the top of the charts.
13. **Wishing You Were Here** — 0% (0 votes · score 200/1000)
   The wistful 1974 hit featuring backing vocals from the Beach Boys.
14. **Beginnings** — 0% (0 votes · score 200/1000)
   The exuberant 1971 single showcasing the band's signature horn section.
15. **Look Away** — 0% (0 votes · score 200/1000)
   The band's 1988 number-one breakup ballad and Billboard year-end topper.

Tags: music, rock, 70s, chicago