Cheap flights from Wisconsin to Massachusetts from $88

In general, May is the cheapest month to fly from Wisconsin to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $68. If you aren’t able to travel to Massachusetts during the month of May, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $68.

According to our data, Friday is the cheapest day to fly to Massachusetts from Wisconsin. The lowest ticket price found for a Friday departure recently was $295. 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 Wisconsin because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $419.

Our data shows that the cheapest Wisconsin to Massachusetts flights are usually those with departure times in the afternoon. Our users have found flights to Massachusetts in the afternoon for as low as $261. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $499 on average. Flights to Massachusetts from Wisconsin at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

Fly from Milwaukee-Mitchell to Boston Logan Intl for the best Wisconsin - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $330 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Wisconsin for as low as $221 on momondo.

There are 4 cabin classes available to choose from on Wisconsin 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, United Airlines, and Delta are the most popular carriers operating from Wisconsin to Massachusetts

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Massachusetts from Wisconsin according to our data. American Airlines is the first choice among our users, with 35% 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 Wisconsin and Massachusetts is 104 per day as of June 2026. The most frequent departure time is 11:00AM, with 83% of daily flights leaving at noon.

The number of flights available between Wisconsin and Massachusetts is 730 per week as of June 2026. The most frequent departure day is Wed, with 22% of weekly flights leaving on this day.