Republican front-runner Donald Trump may be in hot water with the Federal Aviation Administration for reportedly flying to campaign stops on an expired airplane registration.

The New York Times reported Tuesday on the expired registration for Trump's Cessna, which he's used to visit cities like Jackson, Miss., and Sioux City, Iowa.

The 1997 Cessna 750 Citation X, which seats eight people, has been used on hundreds of flights since Trump announced he would seek the Republican nomination in June 2015, according to the FAA. 

The Times reports that dozens of those flights, however, were made after Jan. 31 – the day his $5 registration expired.

Trump’s Cessna flew as recently as Monday, when it was used to transport the candidate between La Guardia Airport in Queens and Buffalo, N.Y., for a campaign event.  Three days earlier, it was used to fly to Plattsburgh, N.Y., and to Hartford for political rallies, according to radio transmissions broadcast by the plane that were archived on a flight data website and reviewed by the Times.

Records show the FAA warned Trump the Cessna’s registration was about to expire. On Dec. 1, DJT Operations CX LLC, the limited liability company owned by Trump that operates the Cessna, was issued a “final notice” the registration was about to expire. Three months later on March 1, DJT Operations CX was sent another notice that the registration had expired.

If the FAA decides to pursue the matter, it could slap a fine on Trump – and possibly even seek prison time, though that’s unlikely. According to the FAA, flying without a registration could result in a civil penalty of up to $27,500 and a criminal fine of up to $250,000 and three years behind bars.

Asked about the report, Trump spokeswoman Hope Hicks told FoxNews.com, "The standard renewal process is just about complete."

Click for more from The New York Times.  

Fox News' Christopher Snyder contributed to this report.