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Massachusetts

$92+ 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 6/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jun 8 — Jun 151
Mon 6/8
Mon 6/15
1 adult, Economy
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Cheap 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 May 9, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:41 am
MKE
-
BOS
Nonstop2h 19m
JetBlue
Wed 6/106:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/5$182
This JetBlue deal was found by Cheapflights users on 5/5. 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 6/38:41 am
MKE
-
BOS
Nonstop2h 19m
JetBlue
Sat 6/66:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/5$187
This Expedia deal was found by Cheapflights users on 5/5. 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.
Sat 6/68:41 am
MKE
-
BOS
Nonstop2h 18m
Multiple Airlines
Wed 6/106:00 am
BOS
-
MKE
1 stop6h 13m
Multiple Airlines
Deal found 5/5$189
This Frontier deal was found by Cheapflights users on 5/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/312:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Wed 6/106:00 am
BOS
-
MKE
1 stop6h 13m
Frontier
Deal found 5/6$190
This Expedia deal was found by Cheapflights users on 5/5. 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.
Wed 6/312:09 pm
MKE
-
BOS
1 stop12h 15m
Multiple Airlines
Wed 6/106:15 am
BOS
-
MKE
Nonstop2h 36m
Multiple Airlines
Deal found 5/5$194
This flugladen.de deal was found by Cheapflights users on 5/5. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:41 am
MKE
-
BOS
Nonstop2h 19m
JetBlue
Mon 6/16:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/5$195
This Delta deal was found by Cheapflights users on 5/5. 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 5/197:50 pm
MKE
-
BOS
Nonstop2h 23m
Delta
Fri 5/225:00 pm
BOS
-
MKE
1 stop6h 28m
Delta
Deal found 5/5$197
This Cheapflightsfares deal was found by Cheapflights users on 5/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:41 am
MKE
-
BOS
Nonstop2h 19m
JetBlue
Mon 6/16:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/6$202
This United Airlines deal was found by Cheapflights users on 5/9. 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 5/305:29 pm
MKE
-
BOS
1 stop4h 52m
United Airlines
Wed 6/36:00 am
BOS
-
MKE
1 stop4h 57m
United Airlines
Deal found 5/9$203
This Frontier deal was found by Cheapflights users on 5/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:10 pm
MKE
-
BOS
1 stop12h 13m
Frontier
Wed 7/296:00 am
BOS
-
MKE
1 stop6h 15m
Frontier
Deal found 5/6$204
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Thu 7/27:23 pm
MKE
-
BOS
1 stop4h 51m
United Airlines
Tue 7/77:00 pm
BOS
-
MKE
1 stop5h 34m
United Airlines
Deal found 5/5$205
This United Airlines deal was found by Cheapflights users on 5/6. 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 6/305:29 pm
MKE
-
BOS
1 stop4h 52m
United Airlines
Wed 7/16:43 pm
BOS
-
MKE
1 stop4h 46m
United Airlines
Deal found 5/6$206

Find flight deals from Milwaukee to Massachusetts

Keep the following information in mind while searching for Milwaukee to Massachusetts flight deals. Data was last updated May 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$182
(Cheapflightsfares)

One-way from

$92
(Super.com)

Popular in

February

Cheapest in

September

Average price

$279

Good round-trip deal

$198 or less

Good one-way deal

$128 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. 15% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 9, 2026.
Use the filters below to find and compare flights from Milwaukee to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 7/1

7:23 pm-1:14 am

1 stop4h 51m

Boston Logan Intl

Tue 7/7

6:00 am-9:53 am

1 stop4h 53m

$205

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 6/5

6:35 pm-11:29 pm

1 stop3h 54m

Boston Logan Intl

Sun 6/7

5:30 am-8:51 am

1 stop4h 21m

$227

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 8/20

6:55 pm-10:22 pm

Nonstop2h 27m

Boston Logan Intl

Sun 8/23

5:30 am-8:52 am

1 stop4h 22m

$247

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 9/11

7:35 pm-10:54 pm

Nonstop2h 19m

Boston Logan Intl

Mon 9/14

2:00 pm-8:52 pm

1 stop7h 52m

$257

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 7/2

6:45 pm-12:05 am

1 stop4h 20m

Boston Logan Intl

Wed 7/8

5:00 pm-11:10 pm

2 stops7h 10m

$262

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 7/28

6:59 pm-10:26 pm

Nonstop2h 27m

Boston Logan Intl

Sun 8/2

5:30 am-8:50 am

1 stop4h 20m

$267

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 8/6

4:47 pm-11:59 pm

1 stop6h 12m

Boston Logan Intl

Sun 8/9

5:30 am-8:52 am

1 stop4h 22m

$277

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 7/14

6:00 am-3:40 pm

2 stops8h 40m

Boston Logan Intl

Thu 7/16

8:00 pm-12:15 am

1 stop5h 15m

$292

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 6/6

6:20 am-3:45 pm

2 stops8h 25m

Boston Logan Intl

Tue 6/16

5:00 pm-11:10 pm

2 stops7h 10m

$292

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 10/30

7:00 pm-1:02 am

1 stop5h 02m

Boston Logan Intl

Tue 11/3

6:00 am-5:13 pm

3 stops12h 13m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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

How far ahead should I book a flight from Milwaukee to Massachusetts?

To ensure you get the cheapest price possible for a flight from Milwaukee to Massachusetts, you should look to book at least 74 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, September is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $78). Flying from Milwaukee to Massachusetts in March is currently the most expensive (average of $197). 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 May 9, 2026.

A simple way to save on the total cost of your ticket is to fly from Milwaukee to Massachusetts in the afternoon. If you’re flexible enough to do this you can expect to save up to 46% 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 May 9, 2026.

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

How much does it cost to fly round-trip from Milwaukee to Massachusetts?

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 May 9, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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
4,302 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,302 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,457 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,692 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,978 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,669 reviews
Southwest
8.0
Very good
4,302 reviews

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 United Airlines, Delta, and Southwest fly from Milwaukee to Massachusetts in about 3h 54m. The time it takes to get you to your destination can typically vary by up to 1h 57m. The distance from Milwaukee to Massachusetts is about 857 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 $78 on JetBlue. Other airlines that offer cheap prices include Southwest from $88 and Delta from $98 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 (93%), Delta (93%) or Republic Airways (93%) 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 $225, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Milwaukee-Mitchell - Boston Logan Intl), you can expect to pay $187 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, September is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $78). Flying from Milwaukee to Massachusetts in March is currently the most expensive (average of $197). 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 May 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$88Average$241FlexibilityNo cancel feeOn-time62%
DeltaCheapest$103Average$357FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$258FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$283FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$192Average$343FlexibilityNo cancel feeOn-time69%

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