Cheap flights from Madison to Massachusetts from $156

In general, January is the cheapest month to fly from Madison to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $397. If you aren’t able to travel to Massachusetts during the month of January, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $431.

According to our data, Wednesday is the cheapest day to fly to Massachusetts from Madison. The lowest ticket price found for a Wednesday departure recently was $431. 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, Thursday is the most expensive day to depart from Madison because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $498.

Our data shows that the cheapest Madison to Massachusetts flights are usually those with departure times at noon. Our users have found flights to Massachusetts at noon for as low as $421. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $465 on average. Flights to Massachusetts from Madison in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Madison Truax Field to Boston Logan Intl for the best Madison Truax Field - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $453 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Madison for as low as $365 on momondo.

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

Sun Country Air, Delta, and United Airlines are the most popular carriers operating from Madison Truax Field to Massachusetts

Delta, American Airlines and JetBlue are the top three most popular airlines that fly to Massachusetts from Madison according to our data. Delta is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 5 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

The number of flights available between Madison and Massachusetts is 1 per day as of November 2026. The most frequent departure time is 2:00PM, with 71% of daily flights leaving in the afternoon.

As of November 2026, 8 flights take off from Madison and land in Massachusetts each week. The most common flight departure day for this route is Wed, with 38% of weekly flights taking off on this day.