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Does anybody really know what time it is? On November 3, the answer from Chicago will be “Christmas time,” as that’s the day the band releases a new collection of its happiest holiday tracks.  Greatest Christmas Hits arrives on CD, vinyl, and digital formats from Rhino Records.  On the same date, the label will reissue 2011’s O Christmas Three and bundle together all three of Chicago’s Christmas albums in one slipcased edition.

Chicago – then consisting of founding members Robert Lamm, Lee Loughnane, James Pankow, and Walter Parazaider as well as Bill Champlin, Keith Howland, Tris Imboden, and Jason Scheff – teamed with producer (and E Street Band keyboardist) Roy Bittan for 1998’s Chicago XXV: The Christmas Album.  The first studio album to appear on the band’s own Chicago Records label, The Christmas Album offered renditions of more than a dozen seasonal favorites plus one original song, Lee Loughnane and John Durrill’s “Child’s Prayer.”  Champlin, Scheff, Lamm, and Loughnane all contributed lead vocals to this spirited and brassy collection which reached the top quarter of the Billboard 200 and was certified Gold.

Four years later, in 2002, Chicago joined the Rhino roster and the album was reissued; in 2003, the decision was made to reenter the studio to record another half-a-dozen Christmas songs.  Veteran producer Phil Ramone – who had helmed 1978’s Hot Streets and 1979’s Chicago XIII, the band’s first albums following the death of original guitarist Terry Kath and first albums without James William Guercio at the controls – oversaw new recordings of five more standards and the affecting Bill Champlin/Tamara Champlin original “Bethlehem.”  The original fourteen songs from Chicago XXV were combined with the six new tracks for What’s It Gonna Be, Santa?  Featuring Keith Howland’s first lead vocal for the band (on “Jolly Old Saint Nicholas”), the album peaked at No. 102 and remained on the charts for five weeks.  It, too, was certified Gold.

With heavy radio airplay each holiday season for Chicago’s yuletide offerings, it seemed inevitable that the group would record another Christmas LP.  O Christmas Three arrived on the band’s own Chicago Records II in 2011, again produced by Phil Ramone.  The band’s 22nd studio album and 33rd album overall, it found the band’s lineup changed, with Bill Champlin out and Lou Pardini in.  Drummer Drew Hester made his only appearance on a Chicago album with O Christmas Three.  Again, most of the songs were bona fide Christmas classics, but a couple of originals also appeared: Phil Galdston and Michael Whalen’s “On the Last Night of the Year,” sung by Lamm, and Loughnane and Durrill’s “Rockin’ and Rollin’ on Christmas Day,” led by Loughnane.  There were some surprises such as a cover of NSYNC’s “Merry Christmas, Happy Holidays,” and a number of guest appearances – a rarity on a Chicago album.  Dolly Parton showed up for a revival of Paul McCartney’s “Wonderful Christmastime,” longtime Chicago pals America appeared on the traditional carol “I Saw Three Ships,” Bebe Winans sang lead on the Carpenters classic “Merry Christmas, Darling,” and Steve Cropper played on “Rockin’ and Rollin’ on Christmas Day.”

In 2019, Chicago released their third Christmas album, their final one to date.  Chicago XXXVII: Chicago Christmas reflected a substantially new band lineup and was their first LP since the retirement of founding member Walter Parazaider.  Co-founders Lamm, Loughnane (who also produced the album), and Pankow were joined by Howland and Pardini plus Walfredo Reyes, Jr. (on drums), Ray Herrmann (on woodwinds, replacing Parazaider), Neil Donell (filling Jason Scheff’s vocal role which had initially been taken by Jeff Coffey upon Scheff’s departure from the group), Brett Simons (on bass), and Ramon Yslas (on percussion).  Unlike Chicago’s past Christmas releases, this one was primarily original.  Robert Lamm, Lee Loughnane, James Pankow, and Lou Pardini all contributed new songs; the only covers were an updated “Sleigh Ride,” the traditional “Here We Come A-Caroling,” and a touching “What the World Needs Now Is Love” sung by Robert Lamm.  Chicago Christmas reached No. 1 on the Billboard Holiday Albums chart.

The 13-song compilation Greatest Christmas Hits draws on all four of these releases, blending holiday classics with the band’s original compositions including Robert Lamm and the late Billy Hinsche’s “(Because It’s) Christmastime,” Neil Donell and Don Breithaupt’s “All Over the World,” and Lee Loughnane and John Durrill’s “Merry Christmas, I Love You.”  (It’s not yet clear which version of the latter will be featured, as it was originally released in both Ballad and R&B Versions.)  Dolly Parton is the only guest star, as her duet on “Wonderful Christmastime” has been reprised.

Greatest Christmas Hits and a standalone reissue of O Christmas Three arrive in stores on November 3 from Rhino.  The bundle of What’s It Gonna Be, Santa?, O Christmas Three, and Chicago Christmas is a Rhino webstore exclusive item which will be available on the same day.  You’ll find track listings and pre-order links below for Greatest Christmas Hits and O Christmas Three.

Chicago, Greatest Christmas Hits (Rhino, 2023)

CD: Amazon U.S. / Amazon U.K. / Amazon Canada
LP: Amazon U.S. / Amazon U.K. / Amazon Canada / Barnes & Noble (Exclusive Green Vinyl)

Side One

1. Let It Snow! Let It Snow! Let It Snow!
2. All Over The World
3. White Christmas
4. Have Yourself A Merry Little Christmas
5. Sleigh Ride
6. Winter Wonderland

Side Two

1. Here We Come A-Caroling
2. Rudolph The Red-Nosed Reindeer
3. Merry Christmas, I Love You
4. (Because It’s) Christmastime
5. Wonderful Christmastime (with Dolly Parton)
6. The Christmas Song
7. Christmas Time Is Here

Chicago, O Christmas Three (Chicago Records II, 2011 – reissued Rhino, 2023) (Amazon U.S. / Amazon U.K. / Amazon Canada)

1. Wonderful Christmastime (with Dolly Parton)
2. Rockin’ Around the Christmas Tree
3. I Saw Three Ships (with America)
4. Merry Christmas, Happy Holidays
5. What Are You Doing New Year’s Eve
6. It’s the Most Wonderful Time of the Year
7. I’ll Be Home for Christmas
8. On the Last Night of the Year
9. Merry Christmas, Darling (with Bebe Winans)
10. Rockin’ and Rollin’ on Christmas Day (with Steve Cropper)
11. My Favorite Things
12. O Christmas Tree
13. Jingle Bells
14. Here Comes Santa Claus/Joy to the World