From what we have read it would appear that Puerto Rico would check your license status on the National Driver Register (NDR) and would see that your Illinois license was cancelled. If your license is suspended, revoked, cancelled, etc in another state or US territory you are not normally permitted to obtain a driver's license elsewhere until you take care of your issue in your previous state and get that license reinstated.
The NDR is a central database of information on problems drivers, meaning motorists, whose license is revoked, suspended, canceled or denied or has been convicted of a serious traffic related offense. All 51 US jurisdictions (meaning the 50 states plus the District of Columbia) provide information to the NDR and can search the database for information on drivers applying for a driver's license.
The federal requirement to check applicants against NDR was intended to prevent problem drivers from shopping around for a license meaning a person would go to a different state to get a new driver's license when their current licenses are suspended or revoked.
[Let CarInsurance.com help you find affordable auto insurance now.] We read through National Driver Register, Title 49 (of the United States Code, Chapter 303) and here it notes that when this document mentions "State" it means a State of the United States, the District of Columbia, Puerto Rico, the Virgin Islands, Guam, American Samoa, the Northern Mariana Islands, the Trust Territory of the Pacific Islands, and any other territory or possession of the United States.
From this it appears that PR can check the NDR when a new driver applies for a license. We have read during the first 120 days you are visiting PR as a non-resident you can operate a motor vehicle if you have a valid, un-expired driver's license issued by any state within the United States. For longer stays, or if you become a resident, you would need to obtain a Puerto Rico license.
New residents of PR must obtain a valid Puerto Rico driver's license within 30 days of establishing residency and may register to vote after 30 days. According to the PR Department of Transportation (DTOP), if you are a U.S. Citizen and you have a valid out-of-state license you must provide the following:
- Take an eye exam
- Pass the written exam, (if you are over 25 and your current license has no outstanding violations, the written exam could be waived)
- Internal Revenue Seal of $10.00
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Without a valid license to turn in and a current suspension of your Illinois driver's license you would need to check with the PR's DMV (Directoría Servicios al Conductor also referred to as DISCO) to see if getting a license there is possible or not. The Service Division of DISOC can be contacted at 787- 296-0290.'
If you are able to get a Puerto Rican driver's license than you should be able to insure a car there as well. If not than it would be difficult to get insurance on a vehicle since you would not have a valid license for an insurance company to rate you on. | 
