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$74+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This JetBlue deal was found by Cheapflights users on 1/28. 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 4/294:34 pm
MKE
-
BOS
Nonstop2h 15m
JetBlue
Sat 5/92:44 pm
BOS
-
MKE
Nonstop2h 30m
JetBlue
Deal found 1/28$207
This Priceline deal was found by Cheapflights users on 1/28. 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.
Mon 3/25:30 pm
MKE
-
BOS
1 stop6h 43m
Frontier
Thu 3/511:45 am
BOS
-
MKE
1 stop7h 57m
Frontier
Deal found 1/28$223
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Thu 3/512:10 pm
MKE
-
BOS
1 stop4h 50m
American Airlines
Tue 3/1711:09 am
BOS
-
MKE
1 stop5h 44m
American Airlines
Deal found 1/28$227
This Southwest deal was found by Cheapflights users on 1/27. 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 3/33:45 pm
MKE
-
BOS
1 stop5h 00m
Southwest
Wed 3/41:20 pm
BOS
-
MKE
2 stops8h 50m
Southwest
Deal found 1/27$232
This Southwest deal was found by Cheapflights users on 1/28. 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 5/135:50 am
MKE
-
BOS
2 stops9h 05m
Southwest
Tue 5/199:15 am
BOS
-
MKE
2 stops14h 35m
Southwest
Deal found 1/28$243
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Tue 2/244:39 pm
MKE
-
BDL
1 stop15h 44m
Frontier
Tue 3/310:19 am
BDL
-
MKE
1 stop30h 25m
Frontier
Deal found 1/27$247
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Sun 3/16:00 am
MKE
-
BOS
1 stop6h 03m
American Airlines
Thu 3/56:52 am
BOS
-
MKE
1 stop6h 04m
American Airlines
Deal found 1/28$247
This Southwest deal was found by Cheapflights users on 1/28. 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 3/114:05 pm
MKE
-
BOS
1 stop5h 05m
Southwest
Mon 3/165:15 am
BOS
-
MKE
1 stop5h 25m
Southwest
Deal found 1/28$250
This Delta deal was found by Cheapflights users on 1/27. 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 5/21:30 pm
MKE
-
BOS
Nonstop2h 24m
Delta
Sat 5/99:00 am
BOS
-
MKE
Nonstop2h 44m
Delta
Deal found 1/27$257
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Fri 9/116:22 am
MKE
-
BOS
1 stop4h 10m
American Airlines
Sat 9/199:06 am
BOS
-
MKE
1 stop5h 59m
American Airlines
Deal found 1/28$262
This Delta deal was found by Cheapflights users on 1/28. 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 5/55:33 pm
MKE
-
BDL
1 stop5h 26m
Delta
Tue 5/128:00 am
BDL
-
MKE
1 stop6h 44m
Delta
Deal found 1/28$263
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Wed 3/1112:10 pm
MKE
-
BOS
1 stop5h 52m
American Airlines
Mon 3/165:31 pm
BOS
-
MKE
1 stop6h 36m
American Airlines
Deal found 1/27$263

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(JetBlue)

One-way from

$74
(Frontier)

Popular in

January

Cheapest in

September

Average price

$509

Good round-trip deal

$298 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. 17% potential increase in price ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 29, 2026.
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

Tue 3/3

3:50 pm-9:25 pm

1 stop4h 35m

Boston Logan Intl

Wed 3/4

5:50 am-9:50 am

1 stop5h 00m

$227

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 4/30

7:58 pm-11:21 pm

Nonstop2h 23m

Boston Logan Intl

Sun 5/10

9:00 am-10:44 am

Nonstop2h 44m

$257

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Tue 5/5

10:11 am-4:54 pm

1 stop5h 43m

Hartford Bradley Intl

Tue 5/12

5:48 am-8:41 am

1 stop3h 53m

$263

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 5/6

5:50 am-1:50 pm

2 stops7h 00m

Boston Logan Intl

Sat 5/9

5:25 am-12:00 pm

1 stop7h 35m

$279

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Tue 2/24

4:39 pm-9:23 am

1 stop15h 44m

Hartford Bradley Intl

Tue 3/3

7:55 pm-3:44 pm

2 stops20h 49m

$287

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

$287

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 5/2

5:09 pm-8:24 pm

Nonstop2h 15m

Boston Logan Intl

Mon 5/11

2:09 pm-3:39 pm

Nonstop2h 30m

$287

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 7/7

7:35 pm-10:54 pm

Nonstop2h 19m

Boston Logan Intl

Sat 7/11

9:00 am-10:44 am

Nonstop2h 44m

$292

MilwaukeeAlbany

MKE - ALB

MKEALB

Milwaukee-Mitchell

Tue 2/24

5:55 pm-11:02 pm

1 stop4h 07m

Albany Intl

Sat 2/28

5:30 am-10:30 am

1 stop6h 00m

$297

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 6/16

7:35 pm-10:54 pm

Nonstop2h 19m

Boston Logan Intl

Sun 6/21

9:00 am-10:44 am

Nonstop2h 44m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 50 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, September 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 $117). 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 January 29, 2026.

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 47% 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 January 24, 2026.

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

Weekly flight availability from Milwaukee to Massachusetts

Explore weekly flight availability from Milwaukee to Massachusetts. 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 January 29, 2026.

The most flights from MKE to USMA are scheduled on a Wednesday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

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 January 29, 2026.
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
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,127 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,206 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,891 reviews
Southwest
8.0
Very good
4,267 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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, Delta, and Frontier fly from Milwaukee to Massachusetts in about 2h 23m. The time it takes to get you to your destination can typically vary by up to 13h 21m. 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 American Airlines from $93 and Southwest 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 Republic Airways (83%), Scandinavian Airlines (81%) or KLM (79%) 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 $327, our data shows the cheapest flight currently is $119. When looking at the most popular route, (Milwaukee-Mitchell - Boston Logan Intl), you can expect to pay $207 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 $91). Flying from Milwaukee to Massachusetts in February is currently the most expensive (average of $117). 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$95Average$269FlexibilityNo cancel feeOn-time62%
DeltaCheapest$108Average$344FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$260FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$280FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$304FlexibilityNo cancel feeOn-time69%

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