{NOTE: I am converting all roman numerals to digits, for clarity.}
The Christmas, 1975 release “Chicago 9” sampled material from their 1969 debut through 1974’s “Chicago 7” (except #3). They would continue to hit the Top 40 through 1978, with the first two singles off of “Hot Streets” (aka Chicago 12). After that, though, “Chicago 13” (1979) and 14 (1980), despite containing some fine music, didn’t generate any hits. Columbia Records rounded out their contract with 1981’s “Greatest Hits Vol. II” (now considered Chicago 15), which covered the material from 8-12, plus a few earlier tracks.
The group jumped to Warner Bros. the next year, where albums 16, 17, 18, and 19 came out at two-year intervals and generated another batch of hits. Christmas 1989’s “Greatest Hits 1982-89” (Chicago 20), collected 12 of those.
That would leave 17 charting singles unaccounted for – five of which hit the Top 40.
While Chicago was signed to Warner Bros., their old label made a habit of releasing occasional compilations of old material. To their credit (or perhaps due to legalities), Columbia did not try to title them with roman numerals and disrupt the group’s sequence of studio albums. 1983’s “If You Leave Me Now” overlaps with Chicago 9 and 15 and grabs one charting single (#32 “Another Rainy Day in New York City”) and one which didn’t chart (“Song For You,” their last Columbia single). But 1985’s “Take Me Back to Chicago” is much better: seven charting singles and two album tracks (though the title track was on Chicago 15).
The next compilation, 1991’s “Group Portrait,” did a great job of summarizing the Columbia years – but it left off the underrated (and polarizing) “Street Player,” which didn’t touch the Hot 100 but did reach #91 on the R&B chart in 1979. "Group Portrait" never made it to vinyl and is also non-canonical.
So is the solution just to go with the CD compilations? I don’t think so.
Chicago 23 and 24 were single CDs released in 1997-98, and they leave off a lot of great cuts in favor of some new material (which would hit the Adult Contemporary chart). Chicago 31 (the 40th anniversary hits compilation from 2007) has the same problem. And all the notable cuts from those albums are on 2002’s “Very Best of Chicago” double CD (though even then, they leave out "Street Player," "Gone Long Gone," "Thunder and Lightning" and "Listen").
In 2003, Chicago released “The Box” (#28) followed by 2005’s “Love Songs”; neither one is on vinyl (and the latter is another superfluous rehash).
So, if you must buy vinyl Chicago compilations, stick with 9, 15, 20, and “Take Me Back to Chicago.” This still leaves out four charting Columbia singles (plus one that didn't), four on Warner Bros. (including the generally disowned remake of "25 or 6 to 4"), plus two charting singles released after the 1969-89 golden era (see table below). I would also love to see albums tracks "Where Do We Go from Here," "A Hit by Varèse," "Mississippi Delta City Blues," and "Byblos" included. Maybe they can put out a 60th anniversary boxed set with 9, 15, 20, "Take Me Back" and one extra disc with the material above.
As for new material released after 1989, there's Chicago 21 (1991), 22 (1995, the Big Band album), 30 (2006), 32 (2008, but recorded in 1993), 36 (2014), and 38 (2022... which is Joe Thomas fantasy camp product; look him up). All other releases since 1991 have been compilations, Christmas albums, live albums, or re-recordings.
SINGLES DISCOGRAPHY:
Mar-70: Make Me Smile (#9)
Jun-70: 25 or 6 to 4 (#4)
Oct-70: Does Anybody Really Know What Time It Is? (#7)
Feb-71: Free (#20)
Apr-71: Lowdown (#35)
Jun-71: Beginnings [reissue]/Colour My World (#7)
Sep-71: Questions 67 and 68 [reissue] (#24)/I'm a Man (#49)
Jul-72: Saturday in the Park (#3)
Oct-72: Dialogue (Part I & II) (#24)
Jun-73: Feelin' Stronger Every Day (#10)
Sep-73: Just You 'n' Me (#4)
Feb-74: (I've Been) Searchin' So Long (#9)
Jun-74: Call on Me (#6)
Oct-74: Wishing You Were Here (#11)
Feb-75: Harry Truman (#13)
Apr-75: Old Days (#5)
Aug-75: Brand New Love Affair (Part I and II) (#61)
Jun-76: Another Rainy Day in New York City (#32)
Jul-76: If You Leave Me Now (#1)
Mar-77: You Are on My Mind (#49)
Sep-77: Baby, What a Big Surprise (#4)
Jan-78: Little One (#44)
May-78: Take Me Back to Chicago (#63)
POST-KATH:
Oct-78: Alive Again (#14)
Dec-78: No Tell Lover (#14)
Mar-79: Gone Long Gone (#73)
Aug-79: Must Have Been Crazy (#83)
Oct-79: Street Player (#91 – R&B)*
Jul-80: Thunder and Lightning (#56)
Oct-80: Song for You (n/a)
WARNER BROS. ERA:
May-82: Hard to Say I'm Sorry (#1)
Sep-82: Love Me Tomorrow (#22)
Jan-83: What You're Missing (#81)
Apr-84: Stay the Night (#16)
Jul-84: Hard Habit to Break (#3)
Nov-84: You're the Inspiration (#3)
Feb-85: Along Comes a Woman (#14)
POST-CETERA:
Aug-86: 25 or 6 to 4 [re-recorded] (#48)
Oct-86: Will You Still Love Me? (#3)
Mar-87: If She Would Have Been Faithful... (#17)
Jun-87: Niagara Falls (#91)
May-88: I Don't Wanna Live Without Your Love (#3)
Sep-88: Look Away (#1)
Jan-89: You're Not Alone (#10)
Apr-89: We Can Last Forever (#55)
Nov-89: What Kind of Man Would I Be? (#5)
Jul-90: Hearts in Trouble (#75)
Jan-91: Chasin' the Wind (#39)
