| Sun, Mar 26 | Sammy Kershaw (with Aaron Tipin & Collin Raye) | Rialto Square Theatre-Joliet | |
| Thu, Mar 30 | Matt Stell | Joe's Live-Rosemont | |
| Fri, Apr 7 | Brett Young | Rosemont Theatre | |
| Thu, Apr 13 | John Mellencamp | Chicago Theatre | |
| Thu, Apr 13 | Walker Hayes | Rosemont Theatre | |
| Thu, Apr 20 | Lady A | Chicago Theatre | |
| Sat, May 6 | Luke Combs | Soldier Field | |
| Sat, May 13 | Chase Rice | Gallagher Way at Wrigley Field | |
| Thu, May 18 | The Mavericks | Rialto Square Theatre-Joliet | |
| Fri, Jun 16 | Joe Nichols | Joe's Live-Rosemont | |
| Thu, Jun 22 | Morgan Wallen | Wrigley Field | |
| Fri, Jun 23 | Morgan Wallen 2 | Wrigley Field | |
| Fri, Jun 23 | Stevie Nicks | United Center | |
| Sat, Jul 1 | Shania Twain | Hollywood Casino Amphitheatre | |
| Sat, Jul 8 | Dierks Bentley | Hollywood Casino Amphitheatre | |
| Fri, Jul 28 | Thomas Rhett | United Center | |
| Wed, Aug 9 | Bruce Springsteen & The E Street Band | Wrigley Field | |
| Sat, Aug 12 | Eric Church | Hollywood Casino Amphitheatre | |
| Thu, Aug 24 | Guns N Roses | Wrigley Field | |
| Sat, Sep 9 | Jason Aldean | Hollywood Casino Amphitheatre | |
| Sun, Oct 8 | Bonnie Raitt | Chicago Theatre | |
