| Thu, Sep 12 | Vince Gill | Chicago Theatre | |
| Sat, Sep 14 | Thomas Rhett (with Dustin Lynch and Russell Dickerson) | United Center | |
| Thu, Sep 19 | Jonas Brothers | https://www.unitedcenter.com/events/2019/09/19/jonas-brothers-happiness-begins/ | |
| Sat, Sep 21 | Farm Aid 2019 (with Willie Nelson,John Mellencamp,Neil Young) | Alpine Valley Music Theatre | |
| Sun, Sep 22 | Nitty Grity Dirt Band | Rialto Square Theatre-Joliet | |
| Fri, Sep 27 | Jason Aldean (with Kane Brown and Carly Pearce) | Hollywood Casino Ampitheatre-Tinley Park | |
| Fri, Sep 27 | The Black Keys (with Modest Mouse) | United Center | |
| Sat, Sep 28 | Chase Rice | Vic Theatre | |
| Sat, Oct 5 | Hank Williams Jr. (with Kd Rock) | Hollywood Casino Amphitheatre-Tinley Park | |
| Sun, Oct 13 | Lyle Lovett | Rialto Square Theatre-Joliet | |
| Sat, Oct 19 | Bob Seger & The Silver Bullet Band | United Center | |
| Tue, Oct 29 | Carrie Underwood (with Runaway June & Maddie & Tae) | United Center | |
| Thu, Nov 7 | Trisha Yearwood | Chicago Theatre | |
| Wed, Nov 27 | Cher (with Nile Rodgers & Chic) | United Center | |
| Fri, Dec 13 | Morgan Evans | Joe's On Weed-Chicago | |
| Sun, Dec 22 | Oak Ridge Boys Christmas Show | Rialto Square Theatre-Joliet | |
