Cheap flights from Boston to Madison from $182

The month of January is, on average, the cheapest month to fly to Madison from Boston, with most prices found around $278. If you’re not able to fly to Madison in January, then March is your next best option. Flight prices from Boston to Madison during March average around $379.

The cheapest day to depart from Boston to Madison is on a Wednesday when prices can be found for as low as $431. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Madison on Sunday is $786.

According to our data, the cheapest time of day to fly to Madison is in the evening. momondo users have found flights departing from Boston to Madison in the evening for as low as $440. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Madison is in the morning when prices are around $489.

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

You are more likely to see cheaper flights to Madison from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Madison for around $449 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Madison from Boston for as low as $353 on momondo.

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

No. A direct flight is the cheapest option for a flight between Boston to Madison.

As of November 2026, prices for Boston to Madison flights are approximately 62% more expensive when compared to flights at the same time last year.

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

Delta, American Airlines and JetBlue are the top three most popular airlines that fly to Madison from Boston according to our data. Delta is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Madison. Keep in mind that there are 5 different airlines that fly to Madison on a routine basis, so you have a few additional options to choose from.

1 flights are operational daily from Boston to Madison as of November 2026. The most popular departure time for this route is 8:00PM, with 77% of flights per day taking off in the evening.

8 flights are operational weekly from Boston to Madison as of November 2026. The most popular departure day for this route is Sun, with 25% of flights per week taking off on this day.