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$99+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Jun 18 — Jun 251
Wed 6/18
Wed 6/25
1 adult, Economy
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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 June 13, 2025.

Round-trip from

$157
(JetBlue)

One-way from

$99
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$306

Good round-trip deal

$212 or less

Good one-way deal

$134 or less
From Massachusetts to Milwaukee-Mitchell
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One-way flight from Massachusetts to Milwaukee-Mitchell
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Highest demand for flights based on searches. 15% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Massachusetts to Milwaukee-Mitchell.
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Price to beat on a one-way flight from Massachusetts to Milwaukee-Mitchell.
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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 June 13, 2025.

This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/12:05 pmBOS - MKE
Nonstop2h 28mJetBlue
Tue 10/74:29 pmMKE - BOS
Nonstop2h 21mJetBlue
Deal found 6/11$157
This Delta deal was found by Cheapflights users on 6/11. 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 8/264:25 pmBOS - MKE
Nonstop2h 47mDelta
Wed 9/36:55 pmMKE - BOS
Nonstop2h 23mDelta
Deal found 6/11$167
This Southwest deal was found by Cheapflights users on 6/10. 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 7/84:25 pmBOS - MKE
1 stop7h 00mSouthwest
Wed 7/165:30 pmMKE - BOS
1 stop4h 50mSouthwest
Deal found 6/10$177
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/195:18 pmBOS - MKE
1 stop7h 14mAmerican Airlines
Sun 8/245:00 amMKE - BOS
1 stop4h 24mAmerican Airlines
Deal found 6/12$212
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/308:35 pmBOS - MKE
2 stops22h 30mSpirit Airlines
Fri 7/49:01 amMKE - BOS
1 stop26h 10mSpirit Airlines
Deal found 6/11$220
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/216:20 amBDL - MKE
1 stop3h 30mSpirit Airlines
Fri 7/259:45 amMKE - BDL
1 stop12h 12mSpirit Airlines
Deal found 6/12$221
This United Airlines deal was found by Cheapflights users on 6/10. 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 7/87:04 pmBOS - MKE
1 stop5h 30mUnited Airlines
Wed 7/165:15 amMKE - BOS
2 stops9h 17mUnited Airlines
Deal found 6/10$252
This Delta deal was found by Cheapflights users on 6/13. 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.
Wed 8/65:35 amBDL - MKE
1 stop4h 08mDelta
Sat 8/95:30 pmMKE - BDL
1 stop5h 21mDelta
Deal found 6/13$257
This American Airlines deal was found by Cheapflights users on 6/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/254:13 pmALB - MKE
1 stop7h 51mAmerican Airlines
Wed 8/276:00 amMKE - ALB
1 stop5h 12mAmerican Airlines
Deal found 6/10$257
This Sun Country Air deal was found by Cheapflights users on 6/11. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/312:22 pmBDL - MKE
1 stop28h 13mSun Country Air
Sun 7/66:53 pmMKE - BDL
1 stop14h 10mSun Country Air
Deal found 6/11$265
This Delta deal was found by Cheapflights users on 6/11. 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.
Sat 8/96:10 amALB - MKE
1 stop3h 26mDelta
Tue 8/125:00 pmMKE - ALB
1 stop5h 08mDelta
Deal found 6/11$269
This Southwest deal was found by Cheapflights users on 6/10. 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.
Mon 8/256:00 amALB - MKE
1 stop5h 00mSouthwest
Wed 8/277:35 amMKE - ALB
2 stops6h 35mSouthwest
Deal found 6/10$303

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 June 13, 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

Wed 10/1

2:05 pm-3:33 pm

Nonstop2h 28m

Milwaukee-Mitchell

Tue 10/7

4:29 pm-7:50 pm

Nonstop2h 21m

$157

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 8/26

4:25 pm-6:12 pm

Nonstop2h 47m

Milwaukee-Mitchell

Wed 9/3

6:55 pm-10:18 pm

Nonstop2h 23m

$167

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 7/8

4:25 pm-10:25 pm

1 stop7h 00m

Milwaukee-Mitchell

Wed 7/16

5:30 pm-11:20 pm

1 stop4h 50m

$177

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 8/19

5:18 pm-11:32 pm

1 stop7h 14m

Milwaukee-Mitchell

Sun 8/24

5:00 am-10:24 am

1 stop4h 24m

$212

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Mon 6/30

8:35 pm-6:05 pm

2 stops22h 30m

Milwaukee-Mitchell

Fri 7/4

9:01 am-12:11 pm

1 stop26h 10m

$220

HartfordMilwaukee

BDL - MKE

BDLMKE

Hartford Bradley Intl

Mon 7/21

6:20 am-8:50 am

1 stop3h 30m

Milwaukee-Mitchell

Fri 7/25

9:45 am-10:57 pm

1 stop12h 12m

$221

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 7/8

7:04 pm-11:34 pm

1 stop5h 30m

Milwaukee-Mitchell

Wed 7/16

5:15 am-3:32 pm

2 stops9h 17m

$252

HartfordMilwaukee

BDL - MKE

BDLMKE

Hartford Bradley Intl

Wed 8/6

5:35 am-8:43 am

1 stop4h 08m

Milwaukee-Mitchell

Sat 8/9

5:30 pm-11:51 pm

1 stop5h 21m

$257

AlbanyMilwaukee

ALB - MKE

ALBMKE

Albany Intl

Mon 8/25

4:13 pm-11:04 pm

1 stop7h 51m

Milwaukee-Mitchell

Wed 8/27

6:00 am-12:12 pm

1 stop5h 12m

$257

HartfordMilwaukee

BDL - MKE

BDLMKE

Hartford Bradley Intl

Thu 7/3

12:22 pm-3:35 pm

1 stop28h 13m

Milwaukee-Mitchell

Sun 7/6

6:53 pm-10:03 am

1 stop14h 10m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

Showing 1-10 of 37 results
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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, February is the cheapest month in which you can book a flight from Massachusetts to Milwaukee (average of $280). Flying from Massachusetts to Milwaukee in June is currently the most expensive (average of $376). 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 June 13, 2025.

When flying from Massachusetts to Milwaukee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 June 13, 2025.

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

Rainfall in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Milwaukee ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Milwaukee when rainfall is around 1.4 in.

Temperature in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Milwaukee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated June 13, 2025.
Read through reviews of airlines operating flights from Massachusetts to Milwaukee, such as Southwest, Delta and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,286 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,792 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,286 reviews

Comfort

8.0

Food

7.1

Crew

8.6

Entertainment

7.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $99. Users have also found prices from $102 and $104 on Spirit Airlines and Southwest, 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 WestJet (91%), KLM (87%) and Virgin Atlantic (87%).

  • What are the cheapest flights from Massachusetts to Milwaukee?

    While on average a flight from Massachusetts to Milwaukee is generally $271, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Boston Logan Intl - Milwaukee-Mitchell), you can expect to pay $157 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, February is the cheapest month in which you can book a flight from Massachusetts to Milwaukee (average of $280). Flying from Massachusetts to Milwaukee in June is currently the most expensive (average of $376). 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 Massachusetts?

Book flights to Massachusetts if you plan to visit one of these locations
Mequon
Sheboygan
Oak Creek
Wauwatosa

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Alternative routes for Massachusetts to Milwaukee

See prices for flight routes from nearby airports that may be better suited for you.
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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 June 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$175FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$144Average$298FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$186Average$291FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$186Average$288FlexibilityNo cancel feeOn-time71%
DeltaCheapest$195Average$397FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$206Average$368FlexibilityNo cancel feeOn-time63%

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