Cheap flights from Milwaukee to Massachusetts from $57

In general, September is the cheapest month to fly from Milwaukee to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $248. If you aren’t able to travel to Massachusetts during the month of September, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $258.

According to our data, Friday is the cheapest day to fly to Massachusetts from Milwaukee. The lowest ticket price found for a Friday departure recently was $289. 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, Sunday is the most expensive day to depart from Milwaukee because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $473.

Our data shows that the cheapest Milwaukee 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 $271. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $488 on average. Flights to Massachusetts from Milwaukee 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 Milwaukee-Mitchell - Massachusetts flight prices

You are more likely to see cheaper flights to Massachusetts from Milwaukee when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $332 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Milwaukee for as low as $214 on momondo.

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

Delta, Southwest, and United Airlines are the most popular carriers operating from Milwaukee-Mitchell to Massachusetts

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Massachusetts from Milwaukee according to our data. American Airlines 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 6 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of April 2026, there are 4 flights per day flying from Milwaukee to Massachusetts. The most common time of day flights depart is 12:00PM, with 96% of flights taking off in the afternoon.

The number of flights available between Milwaukee and Massachusetts is 33 per week as of April 2026. The most frequent departure day is Tue, with 21% of weekly flights leaving on this day.