Cheap flights from Madison to Boston from $159

In general, January is the cheapest month to fly from Madison to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $306. If you aren’t able to travel during the month of January, then book flights to Boston from Madison during September instead. Flights to Boston in September, while not as cheap as those in January, still average around $338.

The cheapest day to depart from Madison to Boston is on a Monday when prices can be found for as low as $377. Be sure to avoid booking your departure on a Tuesday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Tuesday is $475.

According to our data, the cheapest time of day to fly to Boston is in the afternoon. momondo users have found flights departing from Madison to Boston in the afternoon for as low as $410. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $599 per ticket.

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

You are more likely to see cheaper flights to Boston from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $405 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Madison for as low as $365 on momondo.

There are 2 cabin classes available to choose from on Madison to Boston flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 12% on your flight if you consider stops on a Madison to Boston flight.

As of June 2026, prices for Madison to Boston flights are approximately 21% cheaper when compared to flights at the same time last year.

United Airlines and Delta are the most popular carriers operating from Madison Truax Field to Boston Logan Intl

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Boston from Madison according to our data. American Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 5 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

Newark (EWR) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

Flights via New York (LGA) offer the lowest average round-trip price of $301.

Flights connecting via Newark (EWR) have the shortest average one-way travel time: 4h 38m.

Newark (EWR) has the shortest average layover time for this route: 1h 04m.

The number of flights available between Madison and Boston is 3 per day as of June 2026. The most frequent departure time is 3:00PM, with 100% of daily flights leaving in the afternoon.

23 flights are operational weekly from Madison to Boston as of June 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.