| 9/3/2016 | Chicago | 17 | at | Case Western Reserve (9-1) | 45 | at TPAC | ||
| 9/17/2016 | Millsaps (3-7,2-6) | 16 | at | Chicago | 35 | |||
| 9/24/2016 | Chicago | 27 | at | Centre (8-2,6-2) | 49 | |||
| 10/1/2016 | Birmingham-Southern (1-9,1-7) | 34 | at | Chicago | 38 | |||
| 10/8/2016 | Chicago | 21 | at | Berry (9-1,7-1) | 28 | |||
| 10/15/2016 | Rhodes (6-4,4-4) | 26 | at | Chicago | 33 | |||
| 10/22/2016 | Chicago | 28 | at | Hendrix (7-3,5-3) | 52 | |||
| 10/29/2016 | Chicago | 49 | at | Sewanee (0-10,0-8) | 30 | |||
| 11/5/2016 | Carnegie Mellon (7-4) | 37 | at | Chicago | 24 | TPAC | ||
| 11/12/2016 | Washington U (8-3,7-1) | 43 | at | Chicago | 34 |
| vs Chicago | vs Other Opponents | Chicago compared to OOs | |
| Record: | 6-4 | 52-40 | |
| Points Scored: | 36.00 | 32.48 | -3.52 |
| Points Allowed: | 30.60 | 29.36 | 1.24 |
| Margin: | 5.40 | 3.12 | -2.28 |
| Total Points: | 66.60 | 61.84 | 4.76 |