Despite their relative proximity to the USA, the Azores have not yet come close to attaining the level of trendiness and popularity that Iceland has reached in recent years. The Portuguese archipelago, located about 850 miles off the coast of mainland Portugal, receives its fair share of European visitors, but options for traveling to the Azores from the USA have historically been very limited.
That has somewhat changed in recent months, but there are still only a couple of direct routes for getting to the Azores from the US. All flights will be in/out of Ponta Delgada (the largest city in the Azores located on São Miguel Island) and once there, SATA offers short flights to each of the eight other Azorean islands.
If you live in New England, then you have the most direct path to getting to the Azores any time of the year. New York, Providence, and Oakland are all additional summer options. If you live anywhere else in the US, you’ll need a connecting flight in one of these cities (or Lisbon).
Azores Airlines also offers nonstop flights from Toronto and Montreal. While finding affordable flights to the Azores can be difficult, particularly in the summer, it isn’t impossible, however, you might have to be flexible in terms of dates.