Cheap flights from Madison to Boston from $125

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 $315.

The cheapest day to depart from Madison to Boston is on a Wednesday when prices can be found for as low as $347. 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 $436.

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 $393. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to Boston, so prices are often more expensive at around $412 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 $394 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 $329 on momondo.

You could potentially save up to 15% on your flight if you consider stops on a Madison to Boston flight.

As of May 2026, prices for Madison to Boston flights are approximately 9% cheaper when compared to flights at the same time last year.

Delta and United Airlines 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 39% 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: 50% 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.