Covering the period from their recovery from the death of Terry Kath onwards, there were a lot of changes to go through and some lacklustre albums too. Hugh had selected the best tracks, and we updated the show with two tracks from the latest album Chicago XXXVIII: Born For This Moment, released in 2022.
Preshow
| Title | Artists | Album | Year |
| Wonderful Christmas Time | Chicago | Chicago XXXIII – O Christmas Three | 2011 |
| I Saw Three Ships | Chicago | Chicago XXXIII – O Christmas Three | 2011 |
| What Are You Doing New Years Eve | Chicago | Chicago XXXIII – O Christmas Three | 2011 |
| I’ll Be Home For Christmas | Chicago | Chicago XXXIII – O Christmas Three | 2011 |
| Chicago | Chicago | Night and Day: Big-Band | 1995 |
| Caravan | Chicago | Night and Day: Big-Band | 1995 |
| Dream a Little Dream of Me | Chicago | Night and Day: Big-Band | 1995 |
| Goody Goody | Chicago | Night and Day: Big-Band | 1995 |
Main 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? | 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 |
| The Mermaid – Sereia Do Mar | Chicago | Chicago XXXVIII | 2022 |
| Our New York Time | Chicago | Chicago XXXVIII | 2022 |
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 |