Chicago 

One day I'll get a chance to do a more comprehensive analysis of Chicago. Until then I'll provide a quick buyers guide.

I have been a casual fan of Chicago since the early 1970's. Back then I had the Greatest Hits and Chicago Transit Authority. Wanting to upgrade my collection I examined first their two-disc anthology, The Very Best of Chicago: Only the Beginning, a fine overview. I then moved on to Group Portrait, an out of print box set, which covers their best period, up through Chicago XIV. 

I never spent much time contemplating Chicago's rhythm section as the soloists and vocals take center stage. I didn't realize how good they are both individually and together. Peter Cetera is a really strong bass player. 

With a variety of compilations, box sets, and remastered albums that include bonus tracks, there are many options to choose from.  Personally, I opted for getting Chicago I, II, III, V, VI, and VII. Of these six essential studio albums, four were double albums. The remastered editions usually include some bonus tracks that are usually worthwhile. I considered Chicago The Box, but it has some single versions where I wanted the album tracks. But more important, there are oodles of key album tracks not on the box set. Also, there is quite a bit of material on the latter few discs from The Box that doesn't interest me. Perhaps one day I'll be able get Chicago IV, the four-disc Live From Carnegie Hall extravaganza, released in 2005 in expanded format. 

Remastered releases - In 2002, Rhino began remastering Chicago's music. The sonic upgrade is noticeable. Not that the previous editions are terrible, rather this is a move from really, really good to superb. Plus there are bonus songs.

Personally, I prefer the early material. Beyond the radio hits, I haven't heard much beyond Chicago XIV, and I don't have an inclination to. Regarding the more jam oriented material within the first three releases, by far, Chicago Transit Authority ranks at the top, but II and III and great too. Chicago IV, their live album that focuses on the first three releases albums may interest you too. Between the next three studio releases we'd recommend them in the following order, VII, V, and VI. Beyond that it is hit and miss for my tastes. 

The Best Of Chicago 40th Anniversary - Press Release
In 40 years, Chicago has done it all -- five consecutive #1 albums, 13 platinum albums, 21 Top 10 singles, a Grammy and a star on the Hollywood Walk Of Fame. Five years after it began restoring the band's extensive catalogue, Rhino Records salutes one of America's best-selling and longest-running bands with a newly compiled, two-CD set that encompasses the group's entire recording history: THE BEST OF CHICAGO: 40TH ANNIVERSARY EDITION.

Spanning Chicago's entire career -- from its 1969 debut Chicago Transit Authority, to 2006's Chicago XXX -- the 30-song, double-disc anthology contains 30 Top 40 radio tracks including a trio of #1 smashes: "Look Away," "Hard To Say I'm Sorry," and the Grammy-winning "If You Leave Me Now." Sequenced chronologically, the first disc features "Make Me Smile," the band's first Top 10 hit, along with "Does Any One Really Know What Time It Is?" and "Beginnings" from the band's debut, "Colour My World" from Chicago II, "Saturday In The Park," from Chicago V and the group's signature "25 Or 6 To 4."

The second disc continues the hit parade with the epic rock ballad "Love Me Tomorrow," plus "You're The Inspiration" and "Hard Habit To Break" from the back-to-back hit albums Chicago 16 (1982) and Chicago 17 (1984) before concluding with the 2006 hit, "Love Will Come Back."

The album's cover art and internal graphics were selected through a fan contest with long-time fan Mark Rosenmeier cover chosen from over 400 entries. Inside, 10 of the runner-up designs are included, which is testament to the power and talent of Chicago's fans. Music journalist Bill DeYoung penned the liner notes, based on new interviews with the band.

Formed in their namesake city in 1967, Chicago's music mixed rock, pop, and jazz in a completely new way, Propelled by innovative horn arrangements, the band's commercial potential was soon apparent; when in 1970 the band hit the charts with its first of 21 Top 10 singles. The group would go on to score five consecutive #1 albums starting in 1972 with Chicago V, and concluding with Chicago IX -- Chicago's Greatest Hits. In a career both influential and extensive, Chicago has sold more than 100 million records and continues to tour every year to SRO audiences.

Compilations
Chicago's two-disc anthology, The Very Best of Chicago: Only the Beginning, is very well done. For a casual fan, it includes all of the major hits as well as many album tracks. One minor drawback is that it uses a lot of single version edits rather than album tracks, particularly with the first album. 

Chicago has several other greatest hits albums that spans different segments of their career. Some target specific periods and could serve as a supplement for certain periods of their career. They also came out with a selection called Love Songs; for fans that are interested in their pop hits this is a nice package. 

Because of the improved sound with the 2002 re-masters, the best two options are the anthology, The Very Best of Chicago: Only the Beginning, or single disc, Love Songs. 

Box sets
In 1990, Chicago released a superb four disc box set called Group Portrait that included only material through Chicago XIV. It includes great liner notes and the song selections are the album tracks, not single edits. It is now out of print, but second hand copies are available. 

In 2002, Rhino came out with another box set entitled, Chicago The Box. This set covered their entire career with an emphasis on the early years, it is five audio CD's and one DVD. The DVD is from the Arie Crown Theatre in 1972, as well as a promotional film from Chicago XIII from 1979. The music isn't necessarily an upgrade over Group Portrait, but its remastering offers better sound. Though, Group Portrait isn't bad. Be aware that several songs are single versions.

From Chicago's website
Chicago The Box
The only comprehensive Chicago boxed set to date covering their entire career! 
*Over 100 career-spanning songs encompassing full album versions, single    edits, greatest hits, band favorites, and more! 
*Includes three previously unreleased tracks from the fan-requested Stone    of Sisyphus project: "All The Years," "Stone Of Sisyphus," and "Bigger        Than Elvis." 
*Includes a bonus DVD with rare live performances from the Arie Crown Theatre in 1972, and a promotional film from Chicago XIII from 1979. 
*Detailed track-by-track information including original credits and chart information. 
*Produced with hands-on involvement from Chicago themselves. 
*Massive deluxe booklet packed with archival photos. 
*In-depth liner notes from two prominent writers: Part 1 by Phil Gallo and Part 2 by A. Scott Galloway. 

Chicago IV Live at Carnegie Hall
Press release excepts
*Classic live Chicago, recorded at their historic week of Carnegie Hall concerts in April 1971. 
*Nearly four hours of remastered music, including a full disc of eight previously unreleased performances. 
*Bonus discoveries include "Listen," "Loneliness Is Just A Word," and "Sing A Mean Tune Kid." 
Plus alternate versions of songs that do appear on the original, including "Introduction," "25 Or 6 To 4," "Southern California Purples," and an April 9 take of "Free Form Intro (Naseltones)" written at sound check that day. 
*Features stellar live versions of the hits "Does Anybody Really Know What Time It Is?," "Lowdown," "25 Or 6 To 4," "Make Me Smile," "Questions 67 And 68," and "Beginnings," 
"A Song For Richard And His Friends" and "Ballet For A Girl In Buchannon." 
*Packaging makes a nod to the original LP release, with an outer cardboard slipcase, four CDs in individual jackets, 32-page booklet with original LP artwork, and mini-reproductions of the three huge posters that were part of the original package. 
*Liner notes by celebrated music writer Don Heckman.