Will he go to jail for driving with no license?

If he never had a license or it was expired, jail is less likely than if he had one that got revoked. if he can get valid for court that would help

Asking about accident I did last year

That's probably futile. You can request a hearing with the sos to contest that you were at fault. That wold stop the suspension if you request it...

Can I receive supervision on my petty speeding offense even though I am within another period of court supervision.

Nothing in the law prevents you from asking.

You won’t be able to do anything with Illinois until 2021 so MO will not license you. This is so because your two convictions means a five year...

You would answer “yes“ because in order to receive court supervision you had to have pled guilty to the crime of DUI

Can I take driving classes to get my speeding ticket off my record?

You can request supervision and should

Any advice on going to court on a no insurance ticket

Bring in proof of insurance and ask for supervision. Be prepared to be required to carry SR 22 insurance which regular insurance does not replace.

What should I do

Get SR22 before court and you will be valid.

I recieved a warning ticket for expired plates, I was told I couldn’t receive the same ticket for this. But another keeps giving

Renew your plates. Problem solved.

I never had a driver's license and I drove and my license got suspended I am older now how do I get my license back I don't hav?

You can't get a license "back" that you never had. Go apply. See what they say.