Learn the Best Chicago Songs on Acoustic Guitar

Songs like "If You Leave Me Now," "Beginnings," "Color My World," and "Saturday In The Park" are all here, along with chord sheets, rhythm tips, and full instructional videos to get you started.

Check out the Chicago overview video to give you an idea on how some of these songs sound on a single acoustic.

Baby What A Big Surprise is a lush, melodic masterpiece that served as the lead single for the 1977 album Chicago XI. Written by Peter Cetera, the song reached number four on the Billboard Hot 100 and became one of the band's most recognizable romantic ballads of the late 70s.

The recording is notable for its sophisticated vocal harmonies, featuring guest backing vocals from Carl Wilson of the Beach Boys and Chaka Khan. The music video is a unique period piece that features the band performing in a desert setting, with the members dressed in safari-style gear, reflecting the adventurous spirit of the era.

This was the last Top 10 hit for the band to feature the guitar work of Terry Kath before his untimely death. The track remains a staple of soft-rock radio, celebrated for its smooth production and Cetera’s signature tenor.

Beginnings is a seminal jazz-rock anthem from the band’s 1969 debut album, Chicago Transit Authority. Written by Robert Lamm, the song was originally released as a single in 1969 but didn't achieve major chart success until it was re-released in 1971, where it reached number seven on the Billboard Hot 100.

The track is famous for its extended acoustic guitar intro and the complex, soaring brass arrangements that defined the band's early identity. While no formal music video exists from 1969, the song’s legacy is preserved through high-energy live performance clips that showcase the band's incredible percussive outro.

Lamm wrote the lyrics while the band was in a transitional phase, moving from their roots in the Chicago club scene to national stardom. It stands as a definitive example of their ability to blend folk-style songwriting with sophisticated jazz instrumentation.

Color My World is one of the most famous "slow dance" songs in music history, originally appearing as part of the "Ballet for a Girl in Buchannon" suite on the 1970 album Chicago (often referred to as Chicago II).

Written by James Pankow, the song reached number seven on the Billboard Hot 100 when it was released as a single in 1971. The track is recognized for its distinctive arpeggiated piano melody and Walter Parazaider’s delicate flute solo, with Terry Kath providing the soulful lead vocals.

Because of its brevity and romantic tone, it became a quintessential choice for weddings and proms throughout the 1970s. While no official music video was produced, the song is synonymous with the band’s peak era of live televised performances.

This song was never intended to be a standalone hit, but its popularity with radio DJs forced the label’s hand.

If You Leave Me Now is a global cultural phenomenon that served as the lead single for the 1976 album Chicago X. Written by Peter Cetera, the song became the band's first number-one hit in both the United States and the United Kingdom, eventually winning two Grammy Awards for Best Pop Vocal Performance and Best Arrangement.

The track marked a significant shift toward a more ballad-oriented sound, featuring a lush orchestral arrangement that included French horns and strings.

The music video is a simple but effective performance-based clip that features the band in the studio, emphasizing the emotional weight of Cetera’s vocal. The song almost didn't make the album because some band members felt it was too "soft" compared to their jazz-rock roots. It remains one of the best-selling singles of all time, celebrated for its timeless melody and universal theme of romantic plea.

Old Days is a nostalgic and rhythmic track that served as the lead single for the 1975 album Chicago VIII. Written by James Pankow, the song reached number five on the Billboard Hot 100 and features a catchy, mid-tempo groove that explores themes of childhood and the passage of time.

The lyrics were inspired by Pankow’s own memories of growing up in the 1950s, name-checking cultural touchstones like comic books and drive-in movies. The music video is a fun and creative clip that features the band performing interspersed with vintage-style footage of baseball games and family outings. Interestingly, the song features a more prominent electric guitar presence than many of their earlier hits, capturing the "stadium rock" energy of the mid-70s.

It stands as a quintessential "memory song" in their catalog, prized for its warmth and its ability to connect with a multi-generational audience.

Saturday In The Park  is a vibrant and joyous anthem that served as the lead single for the 1972 album Chicago V.

Written by Robert Lamm, the song reached number three on the Billboard Hot 100 and was inspired by a real-life stroll Lamm took through Central Park on a Fourth of July weekend. The track is recognized for its infectious piano riff and the alternating lead vocals between Lamm and Peter Cetera.

The Italian line in the song was often misheard by fans, but it actually translates to "celebrating every day." While no formal music video exists from the 1970s, the song’s legacy is defined by its celebratory brass hooks and its portrayal of a peaceful, communal moment.

Will You Still Love Me is a polished and melodic power ballad that served as the second single from the 1986 album Chicago 18. Written by David Foster, Tom Keane, and Richard Baskin, the song reached number three on the Billboard Hot 100 and marked a major success for the band after the departure of Peter Cetera.

The track features Bill Champlin and Jason Scheff sharing lead vocals, showcasing the band’s ability to maintain their hit-making momentum with a new lineup. The music video is a significant artifact of the mid-80s, featuring cinematic lighting and a narrative of the band performing in a stylized, high-tech studio setting.

A unique bit of trivia is that the song was heavily influenced by the "West Coast" pop sound that David Foster helped pioneer. It remains a staple of adult contemporary radio, recognized for its dramatic arrangement and its heartfelt romantic message.

Wishing You Were Here is a lush and atmospheric ballad featured on the 1974 album Chicago VII.

Written by Peter Cetera, the song reached number eleven on the Billboard Hot 100 and is famous for its intricate vocal harmonies provided by Carl Wilson, Dennis Wilson, and Al Jardine of the Beach Boys. This collaboration gave the track a distinctive, airy quality that stood in contrast to the band’s more brass-heavy output. Interestingly, Terry Kath played acoustic guitar and sang the verses, while Cetera handled the soaring bridge.

While no official music video was produced, the song is highly regarded by critics for its sophisticated production and its portrayal of longing and distance. The recording sessions were famously relaxed, with the Beach Boys reportedly dropping by the studio while Chicago was recording in Colorado.