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Massachusetts

$94+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jun 20 — Jun 271
Sat 6/20
Sat 6/27
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 21, 2026.

This United Airlines deal was found by Cheapflights users on 5/17. 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 6/35:39 pm
MKE
-
BOS
1 stop4h 42m
United Airlines
Sat 6/66:00 am
BOS
-
MKE
1 stop4h 57m
United Airlines
Deal found 5/17$187
This Frontier deal was found by Cheapflights users on 5/18. 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 6/1012:08 pm
MKE
-
BOS
1 stop12h 19m
Frontier
Wed 6/176:00 am
BOS
-
MKE
1 stop6h 13m
Frontier
Deal found 5/18$190
This Cheapflightsfares deal was found by Cheapflights users on 5/20. 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
Sun 6/76:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/20$202
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Fri 6/55:39 pm
MKE
-
BOS
1 stop4h 42m
United Airlines
Sun 6/76:00 am
BOS
-
MKE
1 stop4h 57m
United Airlines
Deal found 5/19$203
This CheapOair deal was found by Cheapflights users on 5/16. 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 CheapOair 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
Multiple Airlines
Wed 6/106:00 am
BOS
-
MKE
1 stop6h 13m
Multiple Airlines
Deal found 5/16$204
This JetBlue deal was found by Cheapflights users on 5/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:41 am
MKE
-
BOS
Nonstop2h 19m
JetBlue
Sun 5/316:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/16$206
This United Airlines deal was found by Cheapflights users on 5/20. 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 12/106:00 am
MKE
-
BOS
1 stop5h 47m
United Airlines
Mon 12/149:30 am
BOS
-
MKE
1 stop5h 13m
United Airlines
Deal found 5/20$208
This Frontier deal was found by Cheapflights users on 5/18. 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 6/1012:08 pm
MKE
-
BOS
1 stop12h 19m
Frontier
Sat 6/206:00 am
BOS
-
MKE
1 stop6h 13m
Frontier
Deal found 5/18$209
This Cheapflightsfares deal was found by Cheapflights users on 5/20. 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 6/108:41 am
MKE
-
BOS
Nonstop2h 18m
JetBlue
Wed 6/177:10 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/20$212
This Priceline deal was found by Cheapflights users on 5/18. 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 Priceline 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
Multiple Airlines
Mon 6/86:00 am
BOS
-
MKE
1 stop6h 14m
Multiple Airlines
Deal found 5/18$213
This Mytrip deal was found by Cheapflights users on 5/17. 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.
Thu 6/258:53 am
MKE
-
BDL
1 stop25h 45m
Frontier
Sat 7/48:05 pm
BDL
-
MKE
1 stop12h 53m
Frontier
Deal found 5/17$283
This Booking.com deal was found by Cheapflights users on 5/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:43 am
MKE
-
BDL
1 stop25h 55m
Frontier
Thu 9/108:55 pm
BDL
-
MKE
1 stop23h 20m
Frontier
Deal found 5/19$323

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 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$187
(American Airlines)

One-way from

$94
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$279

Good round-trip deal

$198 or less

Good one-way deal

$123 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. 16% potential increase in price ($65 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 21, 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 6/10

6:09 am-1:12 pm

1 stop6h 03m

Boston Logan Intl

Sat 6/13

6:40 pm-10:29 pm

1 stop4h 49m

$187

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 6/5

5:50 pm-11:25 pm

1 stop4h 35m

Boston Logan Intl

Tue 6/9

5:25 am-10:55 am

2 stops6h 30m

$232

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 8/26

11:31 am-2:59 pm

Nonstop2h 28m

Boston Logan Intl

Mon 8/31

4:00 pm-8:52 pm

1 stop5h 52m

$247

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 6/3

7:15 am-4:00 pm

1 stop7h 45m

Boston Logan Intl

Sun 6/7

5:30 am-8:51 am

1 stop4h 21m

$247

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 8/19

6:00 am-1:21 pm

1 stop6h 21m

Boston Logan Intl

Sun 8/23

5:30 am-8:52 am

1 stop4h 22m

$257

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 7/3

7:20 pm-10:45 pm

Nonstop2h 25m

Boston Logan Intl

Mon 7/6

6:00 am-10:05 am

1 stop5h 05m

$257
Quickest round-trip

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 7/9

6:59 pm-10:26 pm

Nonstop2h 27m

Boston Logan Intl

Thu 7/23

5:30 am-8:50 am

1 stop4h 20m

$257

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 9/9

6:00 am-7:19 pm

2 stops12h 19m

Boston Logan Intl

Thu 9/17

6:00 am-10:00 am

1 stop5h 00m

$272

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 11/7

2:50 pm-11:54 pm

2 stops8h 04m

Boston Logan Intl

Tue 11/10

6:00 am-5:13 pm

3 stops12h 13m

$283

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 9/10

6:00 am-12:24 pm

1 stop5h 24m

Boston Logan Intl

Fri 9/18

5:30 am-8:41 am

1 stop4h 11m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/20

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

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

Currently, April is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $68). 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 21, 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 47% on your trip compared to booking a flight at noon.

How much does it cost to fly round-trip 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 82 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 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 16, 2026.

Travelers seeking maximum savings on their Milwaukee to Massachusetts flight should consider departing on Saturday 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.

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 21, 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
7.9
Good
4,282 reviews

Overall

7.9

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
7.9
Good
4,282 reviews
Southwest
7.9
Good
4,282 reviews

Overall

7.9

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
8,451 reviews
Southwest
7.9
Good
4,282 reviews

Overall

7.9

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
9,746 reviews
Southwest
7.9
Good
4,282 reviews

Overall

7.9

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
2,981 reviews
Southwest
7.9
Good
4,282 reviews

Overall

7.9

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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
11,639 reviews
Southwest
7.9
Good
4,282 reviews

Overall

7.9

Food

7.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

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, Southwest, and Delta fly from Milwaukee to Massachusetts in about 2h 28m. The time it takes to get you to your destination can typically vary by up to 3h 35m. 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 United Airlines from $93 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 (91%), KLM (89%) or Korean Air (86%) 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 $235, our data shows the cheapest flight currently is $93. 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, April is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $68). 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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$89Average$238FlexibilityNo cancel feeOn-time62%
DeltaCheapest$104Average$356FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$287FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$176Average$261FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$192Average$343FlexibilityNo cancel feeOn-time69%

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