A debtor can refile at any time once the first case is dismissed if the debtor did not voluntarily dismiss the case (assuming the judge didn't bar them for 6 months).
There are only 2 trustee's in cook county, 1 in rockford, and 1 in the collar counties, so the chances are good that the debtor would get the same trustee. Cook county has a handful of judges, but the surrounding counties you'll have the same judge in the 2nd case.
Speak to a lawyer as you lose protection against your creditors after 30 days with a 2nd chapter 13 in a years time. If this would be case #3, you get no protection upon filing. This protection can be extended by motion though however. As long as you can show the court a positive change in circumstances, then you will have a great chance at getting the 2nd case confirmed with the court.
