Cheap flights from Massachusetts to Milwaukee from $70

The cheapest month to fly to Milwaukee from Massachusetts is in September. Flight prices, which tend to average around $244, are often lower during this time because this is during the off-season. The month of May is another great option to travel to Milwaukee, with average flight prices from Massachusetts averaging around $281.

According to our data, Wednesday is the cheapest day to fly to Milwaukee from Massachusetts. The lowest ticket price found for a Wednesday departure recently was $265. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. Flights from Massachusetts to Milwaukee on a Sunday will generally be more expensive and average around $445. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

At noon is the cheapest time of day to fly from Massachusetts to Milwaukee when you can find flight prices for as low as $298. Flying to Milwaukee at noon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Milwaukee, so prices are often more expensive at around $353 per ticket.

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

You are more likely to see cheaper flights to Milwaukee from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Milwaukee for around $333 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milwaukee from Massachusetts for as low as $223 on momondo.

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

Frontier, JetBlue, and Delta are the most popular carriers operating from Massachusetts to Milwaukee-Mitchell

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

4 flights are operational daily from Massachusetts to Milwaukee as of March 2026. The most popular departure time for this route is 4:00PM, with 90% of flights per day taking off in the afternoon.

The number of flights available between Massachusetts and Milwaukee is 32 per week as of March 2026. The most frequent departure day is Mon, with 19% of weekly flights leaving on this day.