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?

1

Colour My World

The tender 1970 ballad that became a wedding and prom staple.

1000pts

2

25 or 6 to 4

The 1970 brass-rock anthem built around its iconic descending guitar riff.

964pts

3

Hard Habit to Break

The 1984 Grammy-nominated ballad about lost love.

874pts

4

If You Leave Me Now

The band's 1976 number-one ballad that won a Grammy for Record of the Year.

856pts

5

Just You 'n' Me

The romantic 1973 top-five hit driven by its memorable sax solo.

807pts

6

Does Anybody Really Know What Time It Is?

The reflective 1970 hit opening with its famous flugelhorn intro.

749pts

7

Saturday in the Park

The sunny 1972 single inspired by a July 4th in New York's Central Park.

749pts

8

You're the Inspiration

The 1984 Peter Cetera-led power ballad and adult-contemporary smash.

749pts

9

Old Days

The nostalgic 1975 single celebrating childhood memories.

749pts

10

Make Me Smile

The 1970 horn-fueled hit excerpted from the Ballet for a Girl in Buchannon suite.

681pts

11

Feelin' Stronger Every Day

The uplifting 1973 single co-written by Peter Cetera and James Pankow.

599pts

12

Hard to Say I'm Sorry

The 1982 comeback ballad that returned Chicago to the top of the charts.

599pts

13

Wishing You Were Here

The wistful 1974 hit featuring backing vocals from the Beach Boys.

499pts

14

Beginnings

The exuberant 1971 single showcasing the band's signature horn section.

499pts

15

Look Away

The band's 1988 number-one breakup ballad and Billboard year-end topper.

499pts