Cheap flights from San Diego to Massachusetts from $129

In general, January 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 $296. If you aren’t able to travel to Massachusetts during the month of January, then flying in September is also cheap. Prices for this month can be found on momondo for an average of $331.

According to our data, Saturday is the cheapest day to fly to Massachusetts from San Diego. The lowest ticket price found for a Saturday departure recently was $351. 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, Monday 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 $487.

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 $355. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $474 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 $373 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 $335 on momondo.

There are 4 cabin classes available to choose from on San Diego to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

JetBlue, United Airlines, and Southwest are the most popular carriers operating from San Diego to Massachusetts

JetBlue, Alaska Airlines and Delta 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 7 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of October 2026, 2 flights take off from San Diego and land in Massachusetts each day. The most common flight departure time for this route is 8:00AM, with 39% of daily flights taking off at noon.

16 flights are operational weekly from San Diego to Massachusetts as of October 2026. The most popular departure day for this route is Fri, with 63% of flights per week taking off on this day.