Cheap flights from Milwaukee to Boston from $143

In general, May is the cheapest month to fly from Milwaukee to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $234. If you aren’t able to travel during the month of May, then book flights to Boston from Milwaukee during June instead. Flights to Boston in June, while not as cheap as those in May, still average around $253.

The cheapest day to depart from Milwaukee to Boston is on a Tuesday when prices can be found for as low as $301. 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 Boston on Sunday is $457.

According to our data, the cheapest time of day to fly to Boston is in the afternoon. momondo users have found flights departing from Milwaukee to Boston in the afternoon for as low as $288. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. At noon is when there is more demand to fly to Boston, so prices are often more expensive at around $483 per ticket.

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

You are more likely to see cheaper flights to Boston from Milwaukee when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $340 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Milwaukee for as low as $225 on momondo.

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

Southwest and Delta are the most popular carriers operating from Milwaukee-Mitchell to Boston Logan Intl

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Boston from Milwaukee 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 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.

Chicago (MDW) was the most common stop: 67% of momondo users choosing 1-stop flights on this route connected there.

Flights via Chicago (MDW) offer the lowest average round-trip price of $268.

Flights connecting via Chicago (MDW) have the shortest average one-way travel time: 4h 35m.

Charlotte (CLT) has the shortest average layover time for this route: 1h 09m.

As of October 2026, 5 flights take off from Milwaukee and land in Boston each day. The most common flight departure time for this route is 11:00AM, with 85% of daily flights taking off at noon.

As of October 2026, 36 flights take off from Milwaukee and land in Boston each week. The most common flight departure day for this route is Wed, with 31% of weekly flights taking off on this day.