When it comes to longevity, Chicago has most bands beat. The group formed in 1967, and despite multiple lineup changes in the years since, they’re still recording, still selling out stadiums, and still keeping their fans happy. To date, they’ve recorded 24 studio albums and sold over 100 million records worldwide, making them one of the best-selling groups of all time. Here, we take a deep dive into their discography as we rank all 24 Chicago albums.
24. Twenty 1
By 1991, grunge was happening and bands like Chicago were fast losing their grip on the charts. Twenty 1 didn’t help matters one little bit. The record label’s insistence on the band using material from songwriter Diane Warren created internal difficulties, as did decisions relating to the final mix. Their heart doesn’t sound in it and frankly, we can’t blame them.
23. Chicago XIV
On paper, Chicago XIV should have worked. After all, it had legendary producer Tom Dowd on board. But it didn’t. It’s messy, inconsistent, and still ranks as one of the band’s poorest selling albums to this day. Understandably enough, Colombia decided enough was enough and gave the band $2 million to go away and become someone else’s problem. The band had the last laugh, though, using the money to fund their major comeback, the platinum-selling Chicago 16.
22. Chicago XXX
After the disappointing Twenty 1, Chicago took 15 years to get around to recording another album of original material. Unfortunately, the result made us wish they hadn’t bothered. Chicago XXX is a toothless, messy album that alternates between major misfires (Feel) and songs that sound like rehashed versions of past successes (Caroline, a poor man’s Look Away). Released on March 21, 2006, it plodded to No. 41 on the Billboard 200.
21. Chicago 13
Chicago 13 has a few nice moments. The jazzy Life Is What It Is is lovely, as is Aloha Mama. The problem is, those moments get lost in a sea of disco that sounded dated in 1979 and sounds positively archaic now. The critics hated it, the public didn’t think much better of it, and it became the first Chicago album not to break into the Top 20.
20. Chicago XXXV: The Nashville Sessions
Chicago XXXV: The Nashville Sessions was recorded at The Sound Kitchen in Nashville at various intervals between shows. It consists of a series of new versions of old hits. And that’s it, basically. It’s not a travesty, but it’s all a bit pointless. If you want to compare how Chicago sound now to how they sounded when they first cut the songs, it’s worth a listen. If you’re not that interested in making comparisons, just listen to the originals – you’ll have a better time.
19. Hot Streets
The band’s tenth studio album marked a departure in more ways than one for Chicago. For a start, the album title broke away from the usual roman-numeral business. More significantly, it saw them embrace disco – and not in a small way either. At one point, there’s even an appearance by the Bee Gees. You can’t really blame them for trying something new, but that doesn’t make the result any more listenable. There are a few gems (Alive Again and No Tell Lover both made the Top 20) but not enough to save it. Released in October 1978, it became the first Chicago album since their debut not to reach the US Top 10.
18. Chicago 19
After breaking ties with producer David Foster (a major contributor to the band’s early and mid-’80s renaissance and the co-writer behind hits like Hard to Say I’m Sorry, Stay the Night, and You’re the Inspiration), the band floundered. They started to rely increasingly heavily on outside writers, lost their sense of identity, and began to sound like a completely different band. Chicago 19 had the hits (I Don’t Wanna Live Without Your Love and Look Away) but not the content to sustain an entire album.
17. Chicago XXXII: Stone of Sisyphus
Next up is the infamous ‘lost’ album. Chicago XXXII: Stone of Sisyphus was originally recorded in 1993 with the intention of becoming the band’s eighteenth studio album. But for some reason, the record company shelved the project, a decision that ultimately led to the band parting ways with their company. Fourteen years and ten albums later, the album finally saw the light of day. To say it would have been better had it stayed buried would be unkind, and not entirely just. Some people loved it. Glide Magazine raved about its “wealth of ideas,” claiming that “anyone who remembers the invigorating sound of the original Chicago will find Stone of Sisyphus wholly comparable, if perhaps not it’s complete equal”. Deseret News called it “worth the wait.” Other people were less flattering in their critique.
16. Chicago 18
Chicago 18 is by no means a bad album. David Foster’s magic touch is sorely missed, but on tracks like Niagara Falls and Over and Over, Chicago showed they could still pull a superbly well-crafted tune out of the bag. The problem lies with one song, but that song (a remake of Terry Kath’s 25 or 6 to 4) is so downright awful, we couldn’t in all good conscience place the album any higher than No. 16 on our list.
15. Chicago XXXVI: Now
After years in the creative wilderness, Chicago made a return to form on 2014’s Chicago XXXVI: Now. It’s not what many people would describe as a dramatic return to form, but there’s some good stuff here, not least the easy-going Watching All the Colors and tough-talking Naked in the Garden of Allah. It might not be on a par with their earlier work, but it’s got enough attitude to carry it through.
14. Chicago XI
After Chicago XI, everything changed for Chicago. Terry Kath accidentally shot himself, and their longtime producer James William Guercio departed. But even though both Kath and Guercio are present on the album, it already feels like things are coming to an end, with most of the songs sounding more like solo projects than group efforts. Still, the songs themselves are solid, with Peter Cetera’s Baby, What a Big Surprise and Danny Seraphine’s Little One both standing out as highlights.
13. Chicago VIII
Chicago VIII sounds like the work of a band that’s in danger of losing its identity. The songs are decent, but there’s nothing to connect them, resulting in a disjointed album that aims high but falls just a little short of the mark. It was still a major hit though, peaking at No. 1 on the Billboard 200 on its release in March 1975.
12. Chicago 16
To say Chicago 16 was a commercial hit would be an understatement. Released on June 7, 1982, it was Chicago’s first album since 1978’s Hot Street to go platinum. It made it to No. 9 on the US Billboard 200, No. 44 in the UK, generated a Grammy Award-nominated single (Hard to Say I’m Sorry), and was generally considered their big comeback. It’s a good album, but the diminished role of Robert Lamm is palpable, and would remain so over the coming albums.
11. Chicago 17
Albums don’t get much bigger than Chicago 17. Released on May 14, 1984. it hit No. 4 on the Billboard 200, spawned four Top 20 hits, won three Grammy Awards, and is widely credited as one of the best adult contemporary records of the ’80s. David Foster’s touch is all over it, resulting in an album of finely tuned, elegant songs that tapped into the tastes of a new generation of fans without losing the band’s identity in the process.
10. Chicago XXXIII: O Christmas Three
Chicago’s third collection of Christmas songs – the creatively titled O Christmas Three – is a surprisingly imaginative endeavor. All the classic Christmas hits are there – Rockin’ Around the Christmas Tree, I’ll Be Home for Christmas, Jingle Bells, and O Christmas Tree – but they’ve been treated with enough ingenuity and enthusiasm to sound fresh. There’s a decent crop of originals, as well, not to mention some lovely guest appearances from the likes of Dolly Parton, America, and Steve Cropper.
9. Chicago XXV: The Christmas Album
An album of Christmas songs is rarely hip, and The Christmas Album certainly isn’t that. But it is festive, with a great selection of seasonal favorites to enjoy. E Street Band pianist Roy Bittan’s production is faultless, as is the band’s performance. It might not be groundbreaking, but if you’re in the mood for some festive fun, it’s perfect.
8. Chicago XXXVII: Chicago Christmas
In 2019, Chicago released their most recent collection of Christmas classics. Only three original members feature, but the classic Chicago sound is still very much intact. The songs, which consist primarily of original material, are well-chosen and impeccably produced. A cheerful, highly enjoyable album.
7. Chicago X
The band’s eighth album found them drifting toward a poppier sound. The change in pace went down a storm, resulting in their first No. 1 single (If You Leave Me Now), a number three position on the Billboard 200, and their first Grammy. It also became the first Chicago album to achieve platinum status, an achievement that the record label celebrated by gifting the band a 25-pound bar of pure platinum.
6. Chicago III
Whatever else you think about Chicago, you can’t fault their work ethic, particularly in their early years. In 1971, they dropped Chicago III, their third consecutive double album in less than two years. It’s not faultless, with a little too much experimentation and not enough focus to sustain it for the duration. But there’s still plenty to like, not least Terry Kath’s Top 20 single, Free.
5. Chicago VII
For their sixth studio album, Chicago made a bold choice, shifting away from their signature sound toward a more jazz-oriented focus. It was a surprise move, but a successful one. Released March 11, 1974, Chicago VII reached No. 1 on the Billboard 200 and eventually certified platinum. The support of three Beach Boys on Peter Cetera’s Wishing You Were Here didn’t exactly dampen its appeal, either.
4. Chicago VI
By Chicago VI, Chicago were starting to move toward a softer-edged sound, but as Ultimate Classic Rock notes, there’s still more than enough rock to keep things interesting. Standout tracks include Robert Lamm’s Darlin’ Dear and the No. 10 hit, Feelin’ Stronger Every Day.
3. Chicago V
Chicago V was very much a Robert Lamm affair, with Peter Cetera barely getting a look in. It could have been a problem, but Lamm is in too good a form for it to matter. The songs are consistently excellent, with A Hit by Varese, Dialogue, and the No. 3 hit Saturday in the Park deserving special mention. Released on July 10, 1972, it became a runaway success, peaking at No. 1 on the Billboard 200 (their first album to do so) and reaching No. 24 in the UK.
2. Chicago Transit Authority
The self-titled debut album from Chicago (who in those days were going by the name Chicago Transit Authority) was an outstanding introduction to the band. Adventurous, ambitious, and peppered with enough stellar songs to make seasoned veterans turn green with envy, it won a Grammy nomination for Best New Artist of the Year, spent 171 weeks on the Billboard 200, achieved double-platinum certification, and, in 2014, was inducted into the Grammy Hall of Fame. For a debut album, you really couldn’t ask for more.
1. Chicago II
If Chicago’s debut album was excellent, their second album was pure perfection. Make Me Smile, Colour My World, and 25 or 6 to 4 all became Top 10 hits, but really, all of the songs are single material. There’s not a single weak moment across the entire album – rare for any record, but particularly for the notoriously difficult second album. A triumph, and unquestionably Chigaco’s finest moment.
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