HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Milwaukee

$89+ Cheap flights from Massachusetts to Milwaukee (MKE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Milwaukee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Massachusetts to Milwaukee

Cheapest flights from Massachusetts to Milwaukee
Explore the most affordable flight options available from Massachusetts to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2025.

This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:00 amBOS - MKE
1 stop5h 18mUnited Airlines
Wed 12/35:00 amMKE - BOS
1 stop6h 43mUnited Airlines
Deal found 10/14$192
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/99:10 amBOS - MKE
2 stops6h 58mUnited Airlines
Thu 12/118:40 amMKE - BOS
1 stop4h 40mUnited Airlines
Deal found 10/14$205
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:23 pmBOS - MKE
1 stop5h 20mUnited Airlines
Wed 11/56:05 amMKE - BOS
1 stop5h 39mUnited Airlines
Deal found 10/14$207
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:50 pmBOS - MKE
2 stops9h 35mSouthwest
Wed 11/52:35 pmMKE - BOS
1 stop6h 40mSouthwest
Deal found 10/14$212
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:00 amBOS - MKE
1 stop5h 18mUnited Airlines
Fri 11/72:45 pmMKE - BOS
1 stop6h 04mUnited Airlines
Deal found 10/14$214
This Southwest deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:50 pmBOS - MKE
1 stop5h 35mSouthwest
Wed 12/36:00 amMKE - BOS
2 stops9h 35mSouthwest
Deal found 10/14$217
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:23 pmBOS - MKE
1 stop5h 20mUnited Airlines
Sat 11/13:49 pmMKE - BOS
2 stops6h 53mUnited Airlines
Deal found 10/15$224
This Southwest deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:15 pmBOS - MKE
1 stop5h 15mSouthwest
Fri 12/125:10 pmMKE - BOS
1 stop5h 05mSouthwest
Deal found 10/15$227
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:00 amBOS - MKE
1 stop5h 40mUnited Airlines
Wed 11/58:44 amMKE - BOS
1 stop6h 26mUnited Airlines
Deal found 10/14$243
This United Airlines deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:00 amBOS - MKE
1 stop5h 19mUnited Airlines
Wed 11/197:00 amMKE - BOS
1 stop4h 44mUnited Airlines
Deal found 10/14$244
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amBDL - MKE
1 stop6h 01mDelta
Thu 11/67:11 amMKE - BDL
1 stop7h 50mDelta
Deal found 10/16$282
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:03 amALB - MKE
1 stop5h 58mDelta
Wed 11/56:00 amMKE - ALB
1 stop6h 16mDelta
Deal found 10/13$297

Cheap flight deals from Massachusetts to Milwaukee

Keep the following information in mind while searching for Massachusetts to Milwaukee flight deals. Data was last updated October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$192
(United Airlines)

One-way from

$89
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$296

Good round-trip deal

$228 or less

Good one-way deal

$183 or less
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Milwaukee-Mitchell flights.
Search Deals
From Massachusetts to Milwaukee-Mitchell
Search Deals
One-way flight from Massachusetts to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Milwaukee-Mitchell.
Search Deals
Price to beat on a one-way flight from Massachusetts to Milwaukee-Mitchell.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Milwaukee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 16, 2025.
Use the filters below to find and compare flights from Massachusetts to Milwaukee that are best for you.

Fly from

Massachusetts

Fly to

Milwaukee

Route

Depart

Return

Price

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Thu 11/13

10:25 am-6:10 pm

1 stop8h 45m

Milwaukee-Mitchell

Mon 11/17

2:35 pm-10:15 pm

1 stop6h 40m

$207

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 10/28

6:23 pm-10:43 pm

1 stop5h 20m

Milwaukee-Mitchell

Wed 11/5

7:00 am-12:44 pm

1 stop4h 44m

$207

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Fri 11/14

5:35 am-10:20 am

1 stop5h 45m

Milwaukee-Mitchell

Sun 11/16

5:50 am-11:25 am

1 stop4h 35m

$207

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Wed 11/12

5:35 pm-9:45 pm

1 stop5h 10m

Milwaukee-Mitchell

Fri 11/14

5:55 pm-11:40 pm

1 stop4h 45m

$207

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Fri 11/14

5:22 pm-11:05 pm

1 stop6h 43m

Milwaukee-Mitchell

Sun 11/16

5:00 am-10:18 am

1 stop4h 18m

$252

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Wed 11/12

11:59 am-6:47 pm

2 stops7h 48m

Milwaukee-Mitchell

Wed 11/19

2:45 pm-11:42 pm

2 stops7h 57m

$272

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Thu 2/26

7:45 am-12:35 pm

1 stop5h 50m

Milwaukee-Mitchell

Sun 3/1

6:00 am-1:13 pm

1 stop6h 13m

$280

HartfordMilwaukee

BDL - MKE

BDLMKE

Hartford Bradley Intl

Fri 10/31

6:00 am-11:01 am

1 stop6h 01m

Milwaukee-Mitchell

Thu 11/6

7:11 am-4:01 pm

1 stop7h 50m

$282

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 11/4

5:30 am-11:29 am

2 stops6h 59m

Milwaukee-Mitchell

Sun 11/9

5:00 am-10:34 am

1 stop4h 34m

$282

AlbanyMilwaukee

ALB - MKE

ALBMKE

Albany Intl

Mon 12/15

12:47 pm-8:19 pm

1 stop8h 32m

Milwaukee-Mitchell

Wed 12/17

5:11 pm-12:02 am

1 stop5h 51m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 48 results
1
2
3
...
5

Best time to book a flight from Massachusetts to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Massachusetts with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Milwaukee

What is the cheapest month to book a flight from Massachusetts to Milwaukee?

Currently, November is the cheapest month in which you can book a flight from Massachusetts to Milwaukee (average of $88). Flying from Massachusetts to Milwaukee in December is currently the most expensive (average of $125). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MA to MKE?

Find hourly flight availability from Massachusetts to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 16, 2025.

It’s optimal to fly from Massachusetts to Milwaukee in the evening. By choosing this option you can save up to 47% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Massachusetts to Milwaukee?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Milwaukee. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Milwaukee flight should consider departing on Monday mornings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Massachusetts to Milwaukee

Explore weekly flight availability from Massachusetts to Milwaukee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 16, 2025.

The most flights from USMA to MKE are scheduled on a Thursday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Milwaukee from Massachusetts?

    If you book a flight to Milwaukee from Massachusetts, you will be flying to Milwaukee-Mitchell, which is the city’s only airport. Milwaukee-Mitchell (MKE) is located 6.4 mi from the center of Milwaukee.

  • How long is the flight from Massachusetts to Milwaukee?

    Airlines like Southwest, United Airlines, and Delta fly from Massachusetts to Milwaukee in about 5h 20m. The time it takes to get you to your destination can typically vary by up to 3h 25m. The distance from Massachusetts to Milwaukee is about 857 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Massachusetts to Milwaukee one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $104. Users have also found prices from $157 and $162 on Delta and United Airlines, respectively.

  • What are the most popular routes from Massachusetts to Milwaukee?

    The most popular flight routes from Massachusetts to Milwaukee are Boston Logan Intl - Milwaukee-Mitchell, Hartford Bradley Intl - Milwaukee-Mitchell and Albany Intl - Milwaukee-Mitchell.

  • What are the most reliable airlines from Massachusetts to Milwaukee?

    The top 3 most reliable airlines when flying from Massachusetts to Milwaukee are JetBlue (87%), Delta (70%) and Republic Airways (70%).

  • What are the cheapest flights from Massachusetts to Milwaukee?

    While on average a flight from Massachusetts to Milwaukee is generally $372, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Boston Logan Intl - Milwaukee-Mitchell), you can expect to pay $192 for that flight.

  • Can I find deals for flights from Massachusetts to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Milwaukee.

  • Can I find deals for business class flights from Massachusetts to Milwaukee?

    Yes. Cheapflights offers flight deals from Massachusetts to Milwaukee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Massachusetts to Milwaukee?

    Currently, November is the cheapest month in which you can book a flight from Massachusetts to Milwaukee (average of $88). Flying from Massachusetts to Milwaukee in December is currently the most expensive (average of $125). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Oak Creek
New Berlin
Wauwatosa

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Seattle to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Denver to O'Hare Intl flights
John F Kennedy Intl to Minneapolis flights
Philadelphia to O'Hare Intl flights
Boston to O'Hare Intl flights
Ontario to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
LaGuardia to Minneapolis flights
Seattle to Minneapolis flights
Orlando to O'Hare Intl flights
Dallas/Fort Worth to Minneapolis flights
Newark to Minneapolis flights
Raleigh to O'Hare Intl flights
Hobby to O'Hare Intl flights
Tampa to O'Hare Intl flights
Austin to O'Hare Intl flights
Los Angeles to Minneapolis flights
Dulles Intl to Minneapolis flights
Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Love Field to O'Hare Intl flights
Baltimore to Minneapolis flights
Charlotte to O'Hare Intl flights
San Diego to O'Hare Intl flights
Miami to O'Hare Intl flights
Reagan-National to Minneapolis flights
Sky Harbor Intl to Minneapolis flights
John F Kennedy Intl to Milwaukee flights
LaGuardia to Milwaukee flights
Portland to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Newark to Milwaukee flights
Columbus to O'Hare Intl flights
Denver to Minneapolis flights
Philadelphia to Minneapolis flights
Burbank to O'Hare Intl flights
Pittsburgh to O'Hare Intl flights
San Jose to O'Hare Intl flights

Top 6 airlines flying from Massachusetts to Milwaukee

Discover the top 6 airlines that operate flights from Massachusetts to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$294FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$145Average$187FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$298FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$317FlexibilityNo cancel feeOn-time69%
DeltaCheapest$187Average$387FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$206Average$332FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.