The concluding part of our examination of the Chicago band’s evolution was put together by Hugh, who is much more familiar with it than I am, not to mention more accepting. A failing on my part which I came to regret on listening to the selections here, and I’m now re-listening to the whole of Chicago’s history again.
Pre and post show selections were from a Chicago Christmas album (one of four), the 1999 Live in Concert album and from the slightly unrepresentative set of Big Band covers entitled Night and Day, which was assembled in a hurry to cover up for the sudden disfavour shown to Stone of Sisyphus by the record label. We put Stone of Sisyphus back in its proper place as Chicago 22…
The latest Chicago album was released on October 11th 2019 and is their fourth Christmas album, simply titled Chicago Christmas. Were it to be numbered, it would be Chicago XXXVII. It was recorded during their 2019 tour using a mobile studio setup, but is not a live album.
Preshow
| Title | Artists | Album | Year |
| Chicago | Chicago | Night and Day: Big-Band | 1995 |
| I Saw Three Ships | Chicago | Chicago XXXIII – O Christmas Three | 2011 |
| Caravan | Chicago | Night and Day: Big-Band | 1995 |
| I’ll Be Home For Christmas | Chicago | Chicago XXXIII – O Christmas Three | 2011 |
| Wonderful Christmas Time | Chicago | Chicago XXXIII – O Christmas Three | 2011 |
| Goody Goody | Chicago | Night and Day: Big-Band | 1995 |
| Dream a Little Dream of Me | Chicago | Night and Day: Big-Band | 1995 |
| What Are You Doing New Years Eve | Chicago | Chicago XXXIII – O Christmas Three | 2011 |
The Show
| Alive Again | Chicago | Hot Streets | 1978 |
| Street Player | Chicago | Chicago 13 | 1979 |
| Upon Arrival | Chicago | Chicago XIV | 1980 |
| Manipulation | Chicago | Chicago XIV | 1980 |
| Waiting For You To Decide | Chicago | Chicago 16 | 1982 |
| Hard To Say I’m Sorry/Get Away | Chicago | Chicago 16 | 1982 |
| Along Comes A Woman | Chicago | Chicago 17 | 1984 |
| We Can Stop The Hurtin’ | Chicago | Chicago 17 | 1984 |
| Forever | Chicago | Chicago 18 | 1986 |
| Niagra Falls | Chicago | Chicago 18 | 1986 |
| Look Away | Chicago | Chicago 19 | 1988 |
| Heart In Pieces | Chicago | Chicago 19 | 1988 |
| Only Time Can Heal The Wounded | Chicago | Chicago 21 | 1991 |
| You Come To My Senses | Chicago | Chicago 21 | 1991 |
| Mah-Jong | Chicago | Chicago XXXII: Stone of Sisyphus | 2008 |
| Bigger Than Elvis | Chicago | Chicago XXXII: Stone of Sisyphus | 2008 |
| Mongonucleosis | Chicago | Chicago XXVI Live In Concert | 1999 |
| Hard Habit To Break | Chicago | Chicago XXVI Live In Concert | 1999 |
| Where Were You?+B78 | Chicago | Chicago XXX | 2006 |
| Feel (Horn Section Mix) | Chicago | Chicago XXX | 2006 |
| Naked In The Garden Of Allah | Chicago | Chicago XXXVI – Now | 2014 |
| Now | Chicago | Chicago XXXVI – Now | 2014 |
Postshow
| Night & Day | Chicago | Night and Day: Big-Band | 1995 |
| Sing, Sing, Sing | Chicago | Night and Day: Big-Band | 1995 |
| In the Mood | Chicago | Night and Day: Big-Band | 1995 |
| Take the ‘A’ Train | Chicago | Night and Day: Big-Band | 1995 |
| Back To You | Chicago | Chicago XXVI Live In Concert | 1999 |
| If I Should Ever Lose You | Chicago | Chicago XXVI Live In Concert | 1999 |
| (Your Love Keeps Lifting Me) Higher & Higher | Chicago | Chicago XXVI Live In Concert | 1999 |