I don't see anything "technical" about his driving illegally or your supporting his unconcern about it. I would not ride with him until he renews his license.

Ask him which he prefers, a day to get his license or no license (won't be allowed to get one, his will be "suspended"), fines, and/or jail and a criminal record.

Driving Without a License Illinois | 625 ILCS 5/6-101 | No DL