Cheap flights from Wisconsin to Boston from $104

In general, May is the cheapest month to fly from Wisconsin to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $308. If you aren’t able to travel during the month of May, then book flights to Boston from Wisconsin during August instead. Flights to Boston in August, while not as cheap as those in May, still average around $325.

The cheapest day to depart from Wisconsin to Boston is on a Saturday when prices can be found for as low as $298. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $460.

According to our data, the cheapest time of day to fly to Boston is in the afternoon. momondo users have found flights departing from Wisconsin to Boston in the afternoon for as low as $294. 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 $471 per ticket.

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

You are more likely to see cheaper flights to Boston from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $341 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Wisconsin for as low as $241 on momondo.

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

Southwest, Delta, and American Airlines are the most popular carriers operating from Wisconsin to Boston Logan Intl

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Boston from Wisconsin according to our data. American Airlines is the first choice among our users, with 38% 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.

As of October 2026, there are 7 flights per day flying from Wisconsin to Boston. The most common time of day flights depart is 11:00AM, with 71% of flights taking off at noon.

50 flights are operational weekly from Wisconsin to Boston as of October 2026. The most popular departure day for this route is Mon, with 22% of flights per week taking off on this day.