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Massachusetts

$81+ Cheap flights from Milwaukee (MKE) to Massachusetts

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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Find flight deals from Milwaukee to Massachusetts

Cheapest flights from Milwaukee to Massachusetts
Explore the most affordable flight options available from Milwaukee to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 26, 2025.

This Southwest deal was found by Cheapflights users on 11/24. 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 12/148:05 amMKE - BOS
1 stop9h 35mSouthwest
Wed 12/177:20 amBOS - MKE
1 stop5h 20mSouthwest
Deal found 11/24$207
This Southwest deal was found by Cheapflights users on 11/24. 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.
Wed 12/1711:30 amMKE - BOS
2 stops8h 35mSouthwest
Thu 12/185:35 amBOS - MKE
1 stop5h 45mSouthwest
Deal found 11/24$212
This Southwest deal was found by Cheapflights users on 11/23. 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 12/73:45 pmMKE - BOS
1 stop7h 20mSouthwest
Wed 12/108:30 amBOS - MKE
2 stops13h 05mSouthwest
Deal found 11/23$218
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:34 amMKE - BOS
1 stop7h 32mSpirit Airlines
Thu 12/1111:08 amBOS - MKE
1 stop23h 31mSpirit Airlines
Deal found 11/25$240
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:34 amMKE - BOS
1 stop7h 32mSpirit Airlines
Wed 12/108:11 pmBOS - MKE
1 stop14h 28mSpirit Airlines
Deal found 11/25$251
This Southwest deal was found by Cheapflights users on 11/24. 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 12/226:30 pmMKE - BOS
1 stop4h 40mSouthwest
Mon 12/296:40 amBOS - MKE
1 stop4h 45mSouthwest
Deal found 11/24$252
This Expedia deal was found by Cheapflights users on 11/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:15 pmMKE - BOS
1 stop12h 46mSpirit Airlines
Tue 12/3012:29 pmBOS - MKE
1 stop7h 51mSpirit Airlines
Deal found 11/25$264
This Southwest deal was found by Cheapflights users on 11/24. 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 12/143:45 pmMKE - BOS
1 stop7h 20mSouthwest
Sun 1/186:50 amBOS - MKE
2 stops12h 35mSouthwest
Deal found 11/24$268
This Southwest deal was found by Cheapflights users on 11/25. 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 12/156:00 amMKE - BOS
2 stops9h 35mSouthwest
Mon 12/155:35 pmBOS - MKE
1 stop5h 10mSouthwest
Deal found 11/25$272
This American Airlines deal was found by Cheapflights users on 11/25. 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.
Sat 12/133:52 pmMKE - BOS
1 stop7h 21mAmerican Airlines
Wed 12/177:20 amBOS - MKE
1 stop5h 44mAmerican Airlines
Deal found 11/25$277
This Kiwi.com deal was found by Cheapflights users on 11/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1110:34 amMKE - BDL
1 stop24h 50mMultiple Airlines
Sun 12/142:03 pmBDL - MKE
1 stop20h 36mMultiple Airlines
Deal found 11/26$278
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/197:21 pmMKE - BOS
1 stop13h 40mMultiple Airlines
Tue 12/3012:29 pmBOS - MKE
1 stop7h 51mMultiple Airlines
Deal found 11/25$278

Cheap flight deals from Milwaukee to Massachusetts

Keep the following information in mind while searching for Milwaukee to Massachusetts flight deals. Data was last updated November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$207
(Southwest)

One-way from

$81
(Orbitz)

Popular in

November

Cheapest in

May

Average price

$438

Good round-trip deal

$368 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
Search Deals
From Milwaukee-Mitchell to Massachusetts
Search Deals
One-way flight from Milwaukee-Mitchell to Massachusetts
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Milwaukee-Mitchell to Massachusetts.
Search Deals
Price to beat on a one-way flight from Milwaukee-Mitchell to Massachusetts.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee to Massachusetts 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 November 26, 2025.
Use the filters below to find and compare flights from Milwaukee to Massachusetts that are best for you.

Fly from

Milwaukee

Fly to

Massachusetts

Route

Depart

Return

Price

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sun 12/7

3:45 pm-12:05 am

1 stop7h 20m

Boston Logan Intl

Wed 12/10

5:35 pm-9:45 pm

1 stop5h 10m

$207

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 1/14

3:45 pm-9:45 pm

1 stop5h 00m

Boston Logan Intl

Wed 1/21

6:50 am-2:00 pm

1 stop8h 10m

$207

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 12/17

11:30 am-9:05 pm

2 stops8h 35m

Boston Logan Intl

Thu 12/18

5:35 am-10:20 am

1 stop5h 45m

$212

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 12/24

4:05 pm-9:40 pm

1 stop4h 35m

Boston Logan Intl

Mon 12/29

5:35 am-10:25 am

1 stop5h 50m

$252

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 5/1

8:00 am-1:50 pm

1 stop4h 50m

Boston Logan Intl

Tue 5/5

6:00 pm-10:35 pm

1 stop5h 35m

$252

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 5/1

5:00 pm-11:32 pm

1 stop5h 32m

Boston Logan Intl

Tue 5/5

5:05 pm-6:57 pm

Nonstop2h 52m

$253

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 12/17

11:30 am-9:05 pm

2 stops8h 35m

Boston Logan Intl

Fri 12/19

5:35 am-10:25 am

1 stop5h 50m

$257

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sun 12/14

8:05 am-6:40 pm

1 stop9h 35m

Boston Logan Intl

Wed 12/17

12:20 pm-9:25 pm

2 stops10h 05m

$257

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 5/1

4:34 pm-7:49 pm

Nonstop2h 15m

Boston Logan Intl

Mon 5/4

2:09 pm-3:39 pm

Nonstop2h 30m

$267

MilwaukeeAlbany

MKE - ALB

MKEALB

Milwaukee-Mitchell

Sat 2/14

2:00 pm-7:15 pm

1 stop4h 15m

Albany Intl

Wed 2/18

5:50 pm-11:48 pm

1 stop6h 58m

$271

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 58 results
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Best time to book a flight from Milwaukee to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Milwaukee 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 Milwaukee to Massachusetts

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

Currently, January is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $91). Flying from Milwaukee to Massachusetts in February is currently the most expensive (average of $137). 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 MKE to MA?

Find hourly flight availability from Milwaukee to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 26, 2025.

A simple way to save on the total cost of your ticket is to fly from Milwaukee to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 72% on your trip compared to booking a flight at noon.

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

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

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

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated November 26, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Milwaukee to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,003 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,050 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,038 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,905 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Milwaukee to Massachusetts. 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 from for flights from Milwaukee to Massachusetts?

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

  • How popular is this Milwaukee to Massachusetts flight route?

    This flight path from Milwaukee-Mitchell to Massachusetts was viewed by 7 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Milwaukee to Massachusetts?

    Airlines like Southwest, Frontier, and Delta fly from Milwaukee to Massachusetts in about 4h 15m. The time it takes to get you to your destination can typically vary by up to 18h 18m. The distance from Milwaukee to Massachusetts is about 713 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    One-way options have recently been found by users for as low as $104 on Southwest. Other airlines that offer cheap prices include Delta from $136 and United Airlines from $141 one-way.

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

    While some choose either Milwaukee-Mitchell - Hartford Bradley Intl or Milwaukee-Mitchell - Albany Intl, Milwaukee-Mitchell - Boston Logan Intl is the most popular route from Milwaukee to Massachusetts.

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

    No one likes to see their flight delayed. When booking a flight from Milwaukee to Massachusetts consider choosing EL AL (58%), Virgin Atlantic (56%) or KLM (53%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Milwaukee to Massachusetts?

    While on average a flight from Milwaukee to Massachusetts is generally $938, our data shows the cheapest flight currently is $123. When looking at the most popular route, (Milwaukee-Mitchell - Boston Logan Intl), you can expect to pay $164 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee to Massachusetts 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 Milwaukee to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $91). Flying from Milwaukee to Massachusetts in February is currently the most expensive (average of $137). 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.

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Alternative routes for Milwaukee to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Milwaukee to Massachusetts

Discover the top 5 airlines that operate flights from Milwaukee to Massachusetts. 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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$280FlexibilityNo cancel feeOn-time62%
DeltaCheapest$151Average$375FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$261FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$291FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$192Average$313FlexibilityNo cancel feeOn-time69%

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