Initially calling themselves the Chicago Transit Authority, Chicago would be one of the most successful bands. Being a band for over 55 years with over 20 studio albums, including two Christmas albums, Chicago XXV: The Christmas Album and Chicago XXXVII: Chicago Christmas, Chicago has rightfully earned respect within the music industry.
They may not be a “cool” band like The Beatles or the Foo Fighters, but they certainly have written some of the greatest songs ever in music history. With that said, if you’re looking for Chicago albums ranked from worst to best, I’ve taken the time to list and discuss my personal rankings of most of their discography.
Chicago Albums Ranked (Worst to First)
The band Chicago dropped their worst album in 1971, entitled Chicago III. However, just a few short years later in 1984, the band released their best album entitled Chicago 17. With that said, let’s see how the rest of Chicago’s album fall on this countdown list.
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15. Chicago III (1971)
Chicago III is an excellent reminder of how Chicago could always create a unique sound. In this album, they successfully blend the elements of jazz, rock, and pop into one album, making a charming listen for any music lover. Additionally, what I appreciate about this album is the band’s approach to instrumental use. Chicago III uses various types of horns and strings, and it is clear that each band member has contributed to this album.
Favorite song from Chicago: “What Else Can I Say” is my favorite song from Chicago III because of the band’s ability to sing about relatable everyday human experiences. Plus, Peter Cetera’s voice is so smooth and sounds heavenly in this song, which makes me fall in love with this song!
14. Chicago XIV (1980)
Unlike Chicago III, Chicago XIV takes a step away from their jazz-pop sound and enters the realm of pop and electronic music. The usage of various electronic elements, such as synthesizers, makes this album fun and upbeat. This perfectly reflects the trends that were taking place within the music industry, and it only makes sense that Chicago would adapt to this style of music.
Additionally, the songwriting for this album is fun because the band heavily emphasizes pop elements for this album. This led the band to write some catchy songs, such as “Thunder and Lighting” and “Song For You.”
Favorite song from Chicago XIV: From Peter Cetera’s incredible vocal talents to the relatable lyrics, this is why “Where Did The Lovin’ Go” is my favorite song from this album. I love this song’s soft-rock and pop combination, which helps make it catchy.
13. Chicago 13 (1979)
For the 13th-best Chicago album on this list, I have picked Chicago 13! There is something special about hearing Peter Cetera’s voice to the sounds of funk and disco that puts me in a good mood. This is why I think “Street Player” is one of the best opening tracks in a Chicago album. I love how the band mixes up their sound with this album. For example, songs like “Aloha Mama” and “Must Have Been Crazy” are very different-sounding songs, but works very well in this album.
Favorite song from Chicago 13: “Loser With A Broken Heart” is an emotionally evoking song, and Peter Cetera’s delivery of emotion and passion makes this song stand out from the others.
12. Chicago VIII (1971)
What makes this album enjoyable is that the band successfully used various elements in a single song, such as “Brand New Love Affair, Pts. 1 & 2,” a ballad that perfectly exemplifies their attempt to mix jazz, funk, and pop elements. Another great feature presented in this album is the usage of various instrumental uses, such as horns, complex chord progressions, and other methods.
An example is the song “Oh, Thank You Great Spirit,” which has a great mix of pop-funk elements and a gorgeous string playing together at once. This album demonstrates that Chicago is a well-rounded band and can offer a great mixture of music.
Favorite song from Chicago VIII: “Old Days” may be the most popular song on this album, but there Is a reason why. This is because the song is a powerful and upbeat song, where Cetera’s vocal adds a layer of passion and fun.
11. Hot Streets (1978)
This uniquely named album from Chicago was the first to be released following the death of their original guitarist and vocalist, Terry Kath. Hot Streets is a pop and disco-filled album. Although it is evident that Kath is greatly missed in this album, it does not take away how underrated this album is.
Hot Streets encompasses the band’s fantastic ability to create catchy songs while demonstrating their technical skills, such as in the song “Little Miss Lovin.” Also, I feel the band uses Hot Streets as a stepping stone to move forward to more experimental songs, such as “Wish I Could Fly.”
Favorite song from Hot Streets: “Alive Again,” is a fun and uplifting way to start an album. The catchy beat and horn featured in this song make this song such a great song to dance to or brighten up your day.
10. Chicago VI (1973)
Chicago VI is one of the best-produced albums, which reaps several benefits. Through this, the various arrangements and technical talents presented in this band are precise, and every detail can be heard. This demonstrates that the band can create an excellent production using different instruments while diving into other genres of music at the same time.
The lyrics presented in this album are another highlight. Many songs, such as “Jenny” and Feelin’ Stronger Every Day” has some awesome hooks and catchy lyrics, which help make this an enjoyable listen for anyone who loves classic rock and jazz.
Favorite song from Chicago VI: “Just You n’ Me” has some of the sweetest lyrics I have heard from this era of music, which is why it is my favorite song from the album. Peter Cetera’s passionate and loving style of singing this song emphasizes the theme of romance within the lyrics.
9. Chicago XI (1977)
By exploring various themes in this album, Chicago offers something relatable for everyone. The themes it explores make Chicago XI a unique album, such as growth, change, and hometown pride. For example, “Taking Me Back to Chicago” is a song that honors their hometown Chicago, which is a song many locals would love.
Then for love song enthusiasts like myself, songs like “This Time” explores a relationship’s insatiable side. And lastly, Chicago again does an exceptional job of blending different types of music genres with complex technical skills.
Favorite song from Chicago XI: Gorgeously sung by Peter Cetera, “Baby, What a Big Surprise,” is my favorite song. I love the lyrics because it focuses on the disbelief within someone when it comes to love and relationship, which I think we all can relate to at one point or another. Overall, this song is beautifully made from the touching lyrics and lovely melody; it truly captures the essence of love.
8. Chicago II (1970)
Chicago II signified the start of Chicago’s desire to experiment with various instruments, techniques, and styles. And as a lover of rock and pop, I could not be more grateful for the band choosing to move in this direction.
What else I like about this album is that by their desire to be experimental, the band takes listeners on a journey, with each song showcasing a particular strength or highlighting their versatility. This includes the band hovering over the theme of politics, which is presented within the lyrics for the song “It Better End Soon.”
Favorite song from Chicago II: “25 Or 6 To 4,” is my favorite song from this album. This song is a banger, from its powerful energy to its catchy yet cryptic lyrics!
7. Chicago VII (1974)
If there is any album where Chicago decided to showcase a mix of different instruments, genres, and musical techniques, Chicago VII is that album. This album features jazz, soft-rock, funk, and salsa elements, which makes it the most diverse Chicago album to this date. What I enjoy about this album is how it starts with “Prelude to Aire” and jumps to “Aire,” both composed so gracefully that it can put any listener into a trance.
Favorite song from Chicago VII: I will always favor a song from Chicago with Peter Cetera leading at vocals, which is no different for “Call On Me.” However, I appreciate the orchestration presentation in this song, with fits so well with the overall album. Cetera’s smooth vocals alone make this song a delightful listening experience.
6. Chicago V (1972)
This album is widely known to be many fans’ favorite album from Chicago. However, as for myself, it does not even crack my top five.
This album’s strength is its ability to create complex and fusion songs while managing to write catchy lyrics and fun melodies. This album certainly emphasizes the horns, as there are many horn features within this album. This ultimately demonstrates Chicago’s almost perfect ability to combine both rock and jazz genres within their music.
Favorite song from Chicago V: “Saturday in The Park” is a timeless song. It would be disrespectful if I did not name it my favorite song from Chicago V. This song starts with an appealing intro and offers a melodious vibe.
5. Chicago 19 (1988)
When it comes to the band Chicago, I am team Peter Cetera, which makes it hard for me to listen to any Chicago album after Peter Cetera’s departure from the band, but I’ll admit there are a couple of exceptions. Chicago 19 is one of those exceptions.
This album features a delightful mix of rock and pop, which I enjoy. From “Heart in Pieces” to “Look Away,” it shows Chicago’s ability to create a powerful energy that makes it impossible not to sing along.
Favorite song from Chicago 19: “I Don’t Wanna Live Without Your Love,” is that powerful love song that should be on everyone’s playlist. As a massive fan of passionate lyrics, I must say this song is top-tier songwriting. From its empowering tempo and unforgettable lyrics, this song is simply one of the best songs from Chicago.
4. Chicago X (1976)
Chicago X is a classic Chicago album featuring their famous horns, keyboards, and of course, the guitar. Although many fans argued that Chicago decided to ditch their jazz elements to produce a pop album that would sell to the masses, I disagree.
I would say Chicago X signified, yet again, another example of the band’s willingness to adapt and evolve. This album is consistent with its structure and themes, making it enjoyable to listen to. Songs like “Scrapbook” and “Hope for Love” demonstrate how Chicago’s artistic skills are rare.
Favorite song from Chicago X: “If You Leave Me Now,” combination with soft guitar playing and sweet melody combined with Peter Cetera’s euphonious makes this the best song on the album.
3. Chicago 18 (1986)
This is another exception where I loved a Chicago album without Peter Cetera. Chicago 18 was the first album without Peter Cetera, and I thought I could only like something with Cetera, but this album proved me wrong. This album features a heavy pop center sound, which I will always appreciate. Although he is no Peter Cetera, Jason Scheff’s vocal delivery was filled with empowerment and passion.
Despite how much I enjoyed this album, I can’t help but miss Cetera’s songwriting in this album. The lyrics are not my favorite, and the saving grace is the instrumental approach and Scheff’s vocal abilities.
Favorite song from Chicago 18: “Will You Still Love Me?” is a powerful ballad and the only song with meaningful lyrics featured in this album. The song’s sweet melody and the band’s instrumental approach make it delightful.
2. Chicago 16 (1982)
I grew up listening to Chicago all my life, and Chicago 16 was the first Chicago album I remember being exposed to. This album was on repeat in my house growing up and is part of the reason why this album is ranked number two overall.
This album is beautifully crafted compared to the other albums on this list. This album is nostalgic and memorable, from the band’s musical chemistry to the emotionally evoking lyrics. One of the features of this album that make it stand out is the heavy emphasis on love. This album is probably why I am a big fan of songs about love and relationships.
Favorite song from Chicago 16: “Hard to Say I’m Sorry/Get Away” is the first song about love and relationships I can remember hearing. The powerful melody, fantastic guitar solo, and emotionally capturing lyrics make this one of my favorite songs ever.
1. Chicago 17 (1984)
Of course, the final album featuring Peter Cetera would be my favorite Chicago album of all time on this Chicago albums ranked from worst to best list.
This album’s pop and electronic elements make it such a timeless piece. Additionally, the lyrics in this album are the most heartfelt, passionate, and relatable compared to anything Chicago wrote before and after Chicago 17. Also, Cetera’s vocals are at their best in this album, providing his most powerful and emotional delivery with Chicago.
Lastly, Chicago has always excelled in their complex instrumental methods, which is no different in this album. Chicago’s instrumental creativity is at its best in this album, which only adds to the strength of this album.
Favorite song from Chicago 17: I do not care if “You’re the Inspiration” is an overplayed song, but this song is one of the best Chicago songs, according to Billboard. This song is beautiful, and it always fills me with a sense of love and happiness each time I listen to it.
This song has a special place in my heart because of how deep and touching the lyrics are. It also was my parent’s wedding song, so there is that too. Regardless, Peter Cetera sings this song perfectly, which is why I love his work so much.
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This article was written by Justinian and edited by Michael.
