This trivia quiz dives deep into the stories behind some of Chicago’s most iconic tracks, offering fans a chance to test their knowledge while celebrating the music that has stood the test of time. Whether you’re a lifelong fan or new to the band’s rich catalog, this quiz will remind you why Chicago remains one of the most beloved bands in rock history.
From their jazz-rock fusion beginnings to their era-defining ballads, Chicago has crafted a legacy of unforgettable songs that continue to inspire fans across generations. Their blend of powerful horns, heartfelt lyrics, and unparalleled musicianship has produced countless hits that still resonate today.
#1. Which Chicago song, released in 1976, won the band their first Grammy Award?
#2. What Chicago song features the lyrics ‘Waiting for the break of day’?
#3. Which song by Chicago was inspired by a celebration in New York’s Central Park?
#4. What song from Chicago’s *Chicago 16* album became a global hit in 1982?
#5. Which Chicago song, written by Peter Cetera, features the line ‘You’re my inspiration’?
#6. What was Chicago’s first charting single, released in 1969?
#7. Which Chicago song became a Top 10 hit in 1970 and features a piano-driven melody?
#8. What ballad by Chicago became a wedding favorite, thanks to its romantic lyrics?
#9. Which Chicago song reflects on political and social unrest in the 1960s?
#10. What Chicago song from 1974 features a horn-driven arrangement and upbeat tempo?
#11. Which Chicago song became their second Billboard Hot 100 No. 1 hit in 1984?
#12. What Chicago song was performed at the 1988 Olympic Games in Seoul?
#13. Which Chicago song features a duet with The Beach Boys?
#14. What song from *Chicago 17* became the band’s third No. 1 hit?
#15. Which Chicago song reflects on nostalgia and features the line ‘Take me back to a simpler time’?
Results
| User | Score | % |
| 5 / 15 | 33.333333333333% | |
| 6 / 15 | 40% |
Related Quizzes
70s Music Trivia-The Band Chicago Trivia
Related Articles
Chicago: A Truly Amazing Band with Great Music
10 Most Popular Chicago Songs Based on BillBoard
Answer Explanations
Which Chicago song, released in 1976, won the band their first Grammy Award?
If You Leave Me Now earned Chicago their first Grammy Award in 1976 for Best Pop Vocal Performance by a Duo, Group, or Chorus. Written and sung by Peter Cetera, the ballad became a worldwide hit, reaching No. 1 on the Billboard Hot 100. The song’s lush orchestration and heartfelt lyrics remain a signature Chicago track.
What Chicago song features the lyrics “Waiting for the break of day”?
25 or 6 to 4 is one of Chicago’s most iconic songs, written by Robert Lamm and released in 1970. The song’s cryptic title refers to the time of day while composing music, and its driving rhythm and horn section have made it a rock classic. It’s a staple of Chicago’s live performances.
Which song by Chicago was inspired by a celebration in New York’s Central Park?
Saturday in the Park, written by Robert Lamm, was inspired by a Fourth of July celebration in Central Park. The song captures the joy and vibrancy of a summer day, blending Chicago’s signature horns with a catchy melody. It became one of the band’s most successful singles, peaking at No. 3 on the Billboard Hot 100.
What song from Chicago’s Chicago 16 album became a global hit in 1982?
Hard to Say I’m Sorry, written by Peter Cetera and David Foster, marked a shift in Chicago’s sound with its soft rock ballad style. The song became a worldwide hit, reaching No. 1 on the Billboard Hot 100. Its success helped revitalize the band’s career in the 1980s.
Which Chicago song, written by Peter Cetera, features the line “You’re my inspiration”?
You’re the Inspiration is one of Chicago’s most beloved ballads, written by Peter Cetera and David Foster. Released in 1984, the song became a chart-topping hit and a favorite at weddings. Its romantic lyrics and emotive arrangement highlight Cetera’s vocal prowess.
What was Chicago’s first charting single, released in 1969?
Questions 67 and 68 was Chicago’s first charting single, released in 1969. Written by Robert Lamm, the song explores themes of love and relationships with a jazz-rock fusion sound. It introduced audiences to Chicago’s signature style, blending horns with powerful vocals.
Which Chicago song became a Top 10 hit in 1970 and features a piano-driven melody?
Does Anybody Really Know What Time It Is?, written by Robert Lamm, became a Top 10 hit in 1970. The song’s reflective lyrics and jazzy piano intro made it a standout track from their debut album. It remains one of the band’s most enduring and recognizable songs.
What ballad by Chicago became a wedding favorite, thanks to its romantic lyrics?
Colour My World, written by James Pankow, is a tender ballad featuring Terry Kath’s vocals. The song’s simple yet heartfelt piano melody and lyrics made it a popular choice for weddings. It’s often paired with Make Me Smile as part of Chicago’s Ballet for a Girl in Buchannon suite.
Which Chicago song reflects on political and social unrest in the 1960s?
Dialogue (Part I & II), written by Robert Lamm, addresses the political and social upheaval of the 1960s. The song features a conversational duet between Terry Kath and Peter Cetera, discussing optimism and skepticism about the future. Its thought-provoking lyrics and dynamic arrangement make it a Chicago classic.
What Chicago song from 1974 features a horn-driven arrangement and upbeat tempo?
Call on Me, written by Lee Loughnane, became a Top 10 hit in 1974. The song’s catchy melody and prominent horn section showcase Chicago’s signature sound. Its uplifting lyrics and lively arrangement make it a fan favorite from the album Chicago VII.
Which Chicago song became their second Billboard Hot 100 No. 1 hit in 1984?
Hard Habit to Break, released in 1984, became a major hit from the album Chicago 17. Written by Steve Kipner and John Lewis Parker, the song features powerful vocals by Peter Cetera and Bill Champlin. Its heartfelt lyrics and lush production earned it critical acclaim and commercial success.
What Chicago song was performed at the 1988 Olympic Games in Seoul?
Hard to Say I’m Sorry was performed at the 1988 Seoul Olympics, showcasing the band’s global appeal. The song’s universal themes of love and reconciliation made it a fitting choice for the international event. It remains one of Chicago’s most iconic tracks.
Which Chicago song features a duet with The Beach Boys?
Wishing You Were Here features backing vocals by The Beach Boys’ Carl Wilson, Dennis Wilson, and Al Jardine. Released in 1974, the song’s mellow vibe and lush harmonies made it a standout track from Chicago VII. The collaboration highlights Chicago’s versatility and connection to other musical legends.
What song from Chicago 17 became the band’s third No. 1 hit?
Look Away, written by Diane Warren, was a major hit from the album Chicago 19. Released in 1988, the song’s emotional lyrics about heartbreak resonated with audiences. It became Chicago’s third No. 1 single on the Billboard Hot 100.
Which Chicago song reflects on nostalgia and features the line “Take me back to a simpler time”?
Old Days, written by James Pankow, is a nostalgic look back at childhood memories. Released in 1975, the song captures a sense of longing for the past with its catchy melody and horn-driven arrangement. It’s a heartfelt tribute to simpler times and a fan favorite.
