Cheap flights from San Diego to Massachusetts from $139

In general, May is the cheapest month to fly from San Diego to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $98. If you aren’t able to travel to Massachusetts during the month of May, then flying in December is also cheap. Prices for this month can be found on momondo for an average of $110.

According to our data, Wednesday is the cheapest day to fly to Massachusetts from San Diego. The lowest ticket price found for a Wednesday departure recently was $337. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from San Diego because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $481.

Our data shows that the cheapest San Diego to Massachusetts flights are usually those with departure times in the evening. Our users have found flights to Massachusetts in the evening for as low as $336. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $457 on average. Flights to Massachusetts from San Diego in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from San Diego to Boston Logan Intl for the best San Diego - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $365 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from San Diego for as low as $303 on momondo.

Alaska Airlines, JetBlue, and American Airlines are the most popular carriers operating from San Diego to Massachusetts

JetBlue, American Airlines and Alaska Airlines are the top three most popular airlines that fly to Massachusetts from San Diego according to our data. JetBlue is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 8 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of May 2026, 8 flights take off from San Diego and land in Massachusetts each day. The most common flight departure time for this route is 11:00AM, with 55% of daily flights taking off at noon.

58 flights are operational weekly from San Diego to Massachusetts as of May 2026. The most popular departure day for this route is Sat, with 24% of flights per week taking off on this day.