I’d fly NYC to somewhere else and then grab a cheap flight. It looks like your options are into Cologne with a cheap flight to Skopje on German Wings, Dusseldorf cheap flight on Air Germania, or Zurich cand a cheap flight on Helvetic. Try a flexible dates search with Kayak.com or Orbitz using NYC to each of those cities and see what you find. One example I saw was Newark to Cologne 12/27/-1/12 for $577. The German Wings website wouldn’t let me get to the booking stage, ut their low fare calendar showed Cologne to Skopje for 48 euros roundtrip.

Good advice from augustin. I couldn’t find anything better. I am having a hard time finding available seats on Germania, Helvetic, and Germanwings around the times you need, but maybe you’ll have better luck with them. Looks like Malev Hungarian airlines have some good prices from a lot of cities in Europe via Budapest to Skopje; they’re turning up in regular searches via BookingBuddy.com, et.al.

If you go on 2 tickets, keep in mind the risk that you assume — if Airline 1 gets you there too late for whatever reason, Airline 2 does not—and most likely will not—accomodate you. Under best circumstances, I’d say leave at least 4 hours. With transatlantic connections, consider 1 day + 4 hours (ie, overnight on arrival and night before return in Cologne or wherever you end up connecting through).

If it’s all on one ticket—such as the $1000+ coming back from BookingBuddy, etc.—then you would most likely be accomodated for a mis-connection.

Hmm, I can’t find any CGN-SKP flights on German Wings after the last week of October, so maybe they don’t fly the route during winter.

That would not surprise me. It is a small airport. I went there with Adria, mostly because they had the best fare at the time, and I recall Malev, Austrian Air and a couple other airlines were also there.