Cheap flights from Boston to Milwaukee from $99

The cheapest month to fly to Milwaukee from Boston is in August. Flight prices, which tend to average around $277, 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 Boston averaging around $277.

According to our data, Saturday is the cheapest day to fly to Milwaukee from Boston. The lowest ticket price found for a Saturday departure recently was $278. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. Flights from Boston to Milwaukee on a Monday will generally be more expensive and average around $458. 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 Boston to Milwaukee when you can find flight prices for as low as $285. Flying to Milwaukee at noon is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Milwaukee, so prices are often more expensive at around $379 per ticket.

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

You are more likely to see cheaper flights to Milwaukee from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Milwaukee for around $337 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Milwaukee from Boston for as low as $291 on momondo.

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

You could potentially save up to 9% on your flight if you consider stops on a Boston to Milwaukee flight.

As of August 2026, prices for Boston to Milwaukee flights are approximately 1% more expensive when compared to flights at the same time last year.

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

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Milwaukee from Boston according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Milwaukee. Keep in mind that there are 5 different airlines that fly to Milwaukee on a routine basis, so you have a few additional options to choose from.

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

Flights via Chicago (ORD) offer the lowest average round-trip price of $198.

Flights connecting via Chicago (ORD) have the shortest average one-way travel time: 5h 07m.

Chicago (ORD) has the shortest average layover time for this route: 0h 59m.

4 flights are operational daily from Boston to Milwaukee as of August 2026. The most popular departure time for this route is 4:00PM, with 52% of flights per day taking off in the afternoon.

30 flights are operational weekly from Boston to Milwaukee as of August 2026. The most popular departure day for this route is Wed, with 27% of flights per week taking off on this day.