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$80+ 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 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Mar 29 — Apr 51
Sun 3/29
Sun 4/5
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 February 27, 2026.

This Frontier deal was found by Cheapflights users on 2/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:13 pm
MKE
-
BOS
1 stop7h 18m
Frontier
Mon 5/46:00 am
BOS
-
MKE
1 stop12h 28m
Frontier
Deal found 2/23$160
This CheapOair deal was found by Cheapflights users on 2/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:34 pm
MKE
-
BOS
Nonstop2h 15m
Multiple Airlines
Mon 5/46:00 am
BOS
-
MKE
1 stop12h 28m
Multiple Airlines
Deal found 2/23$200
This Delta deal was found by Cheapflights users on 2/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/257:25 pm
MKE
-
BOS
Nonstop2h 16m
Delta
Tue 3/314:50 pm
BOS
-
MKE
Nonstop2h 50m
Delta
Deal found 2/24$207
This Southwest deal was found by Cheapflights users on 2/23. 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.
Wed 4/225:50 am
MKE
-
BOS
1 stop4h 10m
Southwest
Wed 4/225:25 pm
BOS
-
MKE
1 stop5h 30m
Southwest
Deal found 2/23$209
This CheapOair deal was found by Cheapflights users on 2/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/155:08 pm
MKE
-
BOS
1 stop6h 43m
Multiple Airlines
Tue 5/192:09 pm
BOS
-
MKE
Nonstop2h 30m
Multiple Airlines
Deal found 2/23$211
This Expedia deal was found by Cheapflights users on 2/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/304:35 pm
MKE
-
BOS
Nonstop2h 15m
Multiple Airlines
Mon 5/46:00 am
BOS
-
MKE
1 stop12h 28m
Multiple Airlines
Deal found 2/23$214
This CheapOair deal was found by Cheapflights users on 2/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1012:03 pm
MKE
-
BOS
1 stop21h 18m
Multiple Airlines
Sat 5/162:44 pm
BOS
-
MKE
Nonstop2h 30m
Multiple Airlines
Deal found 2/25$216
This Delta deal was found by Cheapflights users on 2/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/257:25 pm
MKE
-
BOS
Nonstop2h 16m
Delta
Wed 4/15:30 am
BOS
-
MKE
1 stop4h 20m
Delta
Deal found 2/23$217
This Southwest deal was found by Cheapflights users on 2/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/203:30 pm
MKE
-
BOS
1 stop5h 20m
Southwest
Wed 4/225:45 am
BOS
-
MKE
1 stop4h 55m
Southwest
Deal found 2/26$220
This Delta deal was found by Cheapflights users on 2/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:55 pm
MKE
-
BOS
Nonstop2h 21m
Delta
Thu 6/115:30 am
BOS
-
MKE
1 stop4h 11m
Delta
Deal found 2/24$222
This Delta deal was found by Cheapflights users on 2/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/277:06 am
MKE
-
BOS
1 stop7h 54m
Delta
Sat 5/305:40 am
BOS
-
MKE
1 stop4h 09m
Delta
Deal found 2/23$227
This United Airlines deal was found by Cheapflights users on 2/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/215:37 pm
MKE
-
ALB
1 stop6h 16m
United Airlines
Sat 4/254:55 pm
ALB
-
MKE
1 stop4h 53m
United Airlines
Deal found 2/26$284

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 February 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$160
(Frontier)

One-way from

$80
(Frontier)

Popular in

November

Cheapest in

May

Average price

$321

Good round-trip deal

$277 or less

Good one-way deal

$228 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. 7% potential increase in price ($25 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 February 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 February 27, 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

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 3/17

12:27 pm-3:44 pm

Nonstop2h 17m

Boston Logan Intl

Wed 3/18

4:50 pm-6:40 pm

Nonstop2h 50m

$207

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 4/22

5:50 am-11:00 am

1 stop4h 10m

Boston Logan Intl

Wed 4/22

5:25 pm-9:55 pm

1 stop5h 30m

$209

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 3/17

1:25 pm-7:42 pm

1 stop5h 17m

Boston Logan Intl

Wed 3/18

7:16 am-12:35 pm

1 stop6h 19m

$227

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 5/27

6:00 am-2:15 pm

1 stop7h 15m

Boston Logan Intl

Sat 5/30

5:40 am-8:49 am

1 stop4h 09m

$227

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 3/25

11:00 am-5:19 pm

1 stop5h 19m

Boston Logan Intl

Wed 4/1

6:00 am-10:00 am

1 stop5h 00m

$251

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Mon 3/23

4:20 pm-12:05 am

1 stop6h 45m

Boston Logan Intl

Wed 3/25

5:30 am-9:45 am

1 stop5h 15m

$277

MilwaukeeAlbany

MKE - ALB

MKEALB

Milwaukee-Mitchell

Tue 4/21

5:37 pm-12:53 am

1 stop6h 16m

Albany Intl

Sat 4/25

4:55 pm-8:48 pm

1 stop4h 53m

$284

MilwaukeeAlbany

MKE - ALB

MKEALB

Milwaukee-Mitchell

Wed 3/18

5:49 pm-11:00 pm

1 stop4h 11m

Albany Intl

Sat 3/21

7:00 am-11:06 am

1 stop5h 06m

$297

MilwaukeeAlbany

MKE - ALB

MKEALB

Milwaukee-Mitchell

Thu 5/14

7:10 pm-12:48 am

1 stop4h 38m

Albany Intl

Wed 5/20

4:55 pm-10:33 pm

1 stop6h 38m

$312

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Wed 4/1

6:30 am-1:57 pm

1 stop6h 27m

Hartford Bradley Intl

Sat 4/4

5:34 am-8:46 am

1 stop4h 12m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/25

Showing 1-10 of 59 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, 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 January 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 February 27, 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 45% 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 February 21, 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. Sunday 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 February 27, 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
4,301 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Southwest
8.0
Very good
4,301 reviews
Southwest
8.0
Very good
4,301 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Delta
7.9
Good
8,243 reviews
Southwest
8.0
Very good
4,301 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
United Airlines
7.4
Good
9,349 reviews
Southwest
8.0
Very good
4,301 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
American Airlines
7.2
Good
11,357 reviews
Southwest
8.0
Very good
4,301 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
JetBlue
7.2
Good
2,896 reviews
Southwest
8.0
Very good
4,301 reviews

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

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 Delta, Southwest, and United Airlines fly from Milwaukee to Massachusetts in about 2h 17m. The time it takes to get you to your destination can typically vary by up to 3h. 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 $98 and American Airlines 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 KLM (81%), Republic Airways (76%) or Scandinavian Airlines (75%) 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 $351, our data shows the cheapest flight currently is $98. When looking at the most popular route, (Milwaukee-Mitchell - Boston Logan Intl), you can expect to pay $195 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 January 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 February 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$89Average$268FlexibilityNo cancel feeOn-time62%
DeltaCheapest$107Average$351FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$258FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$280FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$192Average$313FlexibilityNo cancel feeOn-time69%

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