You could in theory end up with three convictions but that's not likely in reality. And if you have never been suspended before even if you get suspended. you would probably qualify for a probationary license.
These matters are all pending at the same time. You are entitled to (2) Court Supervisions in a 12-month period. After you have hit that mark, the appropriate sentence should be a traffic conviction. You can have 2 traffic convictions, after having 2 Court Supervisions and still be fine - a 3rd traffic conviction in any 12-month period will result in a Discretionary Suspension imposed by the Secretary of State that you would receive by mail. You are still not at risk of that happening under your current scenario, because it is unlikely that Cook County will try to violate the first Supervision you received since the court system there is just too congested to violate petty offenses due to subsequent out-of-county traffic stops. You will likely get Court Supervision on one of the two pending tickets and you may receive a traffic conviction on one of them - likely making it so that you would still have to get 2 additional convictions before they suspend your license. It may be wise to seek out counsel to increase your odds that these matters get handled properly.