If mobile phones were as common back when this movie was made as they are today, things would have been different for Neal. Or at the very least, his trip wouldn't have been as troublesome.
And funny enough, there is a cellular phone ad at the L-Train stop at the end of the film. Also worth noting that Neal was probably wealthy enough to afford a mobile phone from the period.
The film Due Date, made in the internet-connected world of 2010 still manages to borrow heavily from this film.
Finding the next flight or the nearest hotel? There's an app for that.
Considering how badly everything else in the movie goes for him, even if Neil did have an internet-accessable device, it'd be long dead by the time the shit started to hit the fan.
Troubled Production: The experience of making the film was not a happy one for John Hughes as many shooting days would either be lost or delayed due to weather issues or having to work around certain loopholes (for example, a sequence involving a train had change shooting locations due to a lack of snow and the crew had to create a train route from scratch as the local train company wouldn't allow them to use theirs). Also, the rough cut ran over three hours and the film spent many months in post-production so to cut the film to a manageable length (this is also why references to Hughes's next film appear, as it has begun production right after this film finished filming). In addition to these problems, Hughes was also smarting over the fact that his long term business relationship with Molly Ringwald had gone sour after she turned down the Lea Thompson role of Amanda Jones in Some Kind of Wonderful. Hughes was so upset over the rejection that he never worked with Ringwald again for the rest of his life.
Unintentional Period Piece: Neal's Cluster F-Bomb includes a demand for a Datsun. Just a couple years earlier Nissan had ditched the "Datsun" name in North America and began marketing their cars under their own name, and a lot of their marketing at the time reflected this. (Indeed, Nissan's slogan in 1987 was, "The Name is Nissan!")