| Sat, Jul 17 | Wynonna Judd | Space-Evanston | |
| Thu, Jul 29 | James Taylor with Jackson Browne | United Center | |
| Sat, Aug 14 | Willie Nelson | Ravinia | |
| Sat, Aug 21 | Luke Bryan (with Dylan Scott & Runaway Joe) | Hollywood Casino Amphitheatre-Tinley Park | |
| Sun, Aug 22 | Dwight Yoakam | Rialto Square Theatre-Joliet | |
| Thu, Aug 26 | Hall & Oates (with K.T. Tunstall & Squeeze) | Hollywood Casino Amphitheatre-Tinley Park | |
| Sat, Aug 28 | Zac Brown Band | Hollywood Casino Amphitheatre-Tinley Park | |
| Fri, Sep 3 | Lady A | Ravinia | |
| Fri, Sep 10 | Brad Paisley | Hollywood Casino Amphitheatre-Tinley Park | |
| Sat, Sep 11 | Blake Shelton (with Martina McBride, Lindsay Ell & Tracy Byrd) | Allstate Arena | |
| Sat, Sep 25 | Thomas Rhett | Hollywood Casino Amphitheatre-Tinley Park | |
| Wed, Sep 29 | Little Big Town | Chicago Theatre | |
| Thu, Sep 30 | Little Big Town 2 | Chicago Theatre | |
| Sat, Oct 2 | Dan and Shay | United Center | |
| Thu, Nov 4 | Luke Combs (with Ashley McBryde) | United Center | |
| Thu, Nov 4 | Gary Allan | Rialto Square Theatre-Joliet | |
| Mon, Nov 15 | Genesis | United Center | |
| Sat, Mar 19 | Reba McEntire | Allstate Arena | |
| Sat, Jul 23 | Chris Stapleton | Wrigley Field | |
