I was caught driving on second DUI while license is revoked and right before my 2 years probationary period was over.

You are looking at a felony on the new case and resentencing on the old case. You need to retain counsel ASAP.

Yes, you can get a DUI on any motorized vehicle.

What are the consequences for receiving a dui while on supervision for a dui, in Illinois.

In addition to the points the others mention (especially that you face a minimum 5 years license revocation if you get 2 convictions), you are...

Was charged with criminal damage to property after stupidly/drunkenly pulling some plants out of a planters box.

This is a criminal offense and a conviction might haunt you for a long time. You should consult with an attorney.

If I ask a judge for supervision on my third speeding ticket is he likely to say yes

Illinois law only allows two supervisions for a moving violation in a year. An attorney might be able to get the charge reduced or dismissed.

My license is revoked due to two DUIs, I need my license reinstated.

You need to clear your license in Illinois before you will eligible to get a license here or anywhere else. You will need to have a reinstatement...

Is it possible to plea to a reduced charge in ski child endangerment in cook county? What kind of offer would I likely get?

Without knowing more about the details of your case, it is impossible to discuss the likelihood of getting the charges reduced or the suspension...

I just received my second dui in 3years what can I do to avoid jail time

You have to worry now about both the old case as well as a violation of the conditions of your old sentence. You need to retain an attorney...

Can a case be reopened?

No, it is too late to re-open your guilty plea.

Driving record, PDPS, and National say I have one DUI on my record yet i have a lifetime revocation. Can this be lifted?

I assume that you mean that you have had four DUI convictions and Illinois won't consider you for reinstatement. If that is so, then it doesn't...