A background shot shows an Amtrak ACS-64 traveling under a bridge. In addition to not being introduced until 2014, the ACS-64 is an electric locomotive powered by overhead lines, and are not run in Chicago, where the movie takes place.
Numerous buildings are visible which were not built in 1999.
The movie takes place in 1999, but James is shown riding a CTA 5000-series train, not introduced until 2011.
Numerous cars which did not exist in 1999 are shown.
The Phreaker says he turned 15 in 1987, and the movie's set in 1999, making him 27. But the actor who plays him is over 40, and clearly looks it.