By Tour Name | By Year | By Venue | By City | By Country/State
Shows by City: Chicago
| Show Date | Venue | City | State | Tour Name | |
| 07-13-2018 | Wrigley Field | Chicago | IL | Son Of A Son Of A Sailor Tour – 2018 | |
| 07-15-2017 | Wrigley Field | Chicago | IL | I Don’t Know Tour – 2017 | |
| 06-16-2016 | House of Blues | Chicago | IL | I Don’t Know Tour – 2016 | |
| 06-27-2015 | First Midwest Bank Amphitheater | Chicago | IL | Workin’ and Playin’ Tour | |
| 06-29-2013 | Charter One Pavilion | Chicago | IL | Songs From St. Somewhere Tour | |
| 09-05-2005 | Wrigley Field | Chicago | IL | A Salty Piece Of Land Tour | |
| 09-04-2005 | Wrigley Field | Chicago | IL | A Salty Piece Of Land Tour | |
| 05-28-1987 | Apollo Theatre | Chicago | IL | A Pirate Looks At Forty Tour | |
| Number of Shows: 8 | |||||