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Massachusetts

$89+ 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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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 July 3, 2025.

Round-trip from

$157
(JetBlue)

One-way from

$89
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$276

Good round-trip deal

$151 or less

Good one-way deal

$108 or less
From Milwaukee-Mitchell to Massachusetts
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One-way flight from Milwaukee-Mitchell to Massachusetts
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Highest demand for flights based on searches. 12% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Milwaukee-Mitchell to Massachusetts.
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Price to beat on a one-way flight from Milwaukee-Mitchell to Massachusetts.
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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 July 3, 2025.

This JetBlue deal was found by Cheapflights users on 7/3. 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 9/275:09 pmMKE - BOS
Nonstop2h 21mJetBlue
Sat 10/42:10 pmBOS - MKE
Nonstop2h 28mJetBlue
Deal found 7/3$157
This Southwest deal was found by Cheapflights users on 7/3. 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.
Thu 8/1412:20 pmMKE - BOS
1 stop4h 40mSouthwest
Mon 8/186:40 amBOS - MKE
1 stop10h 35mSouthwest
Deal found 7/3$177
This United Airlines deal was found by Cheapflights users on 6/30. 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 7/185:31 pmMKE - BOS
1 stop4h 45mUnited Airlines
Sat 7/268:02 pmBOS - MKE
1 stop4h 52mUnited Airlines
Deal found 6/30$202
This Delta deal was found by Cheapflights users on 7/1. 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.
Fri 8/157:55 pmMKE - BOS
Nonstop2h 24mDelta
Mon 8/185:20 pmBOS - MKE
Nonstop2h 54mDelta
Deal found 7/1$208
This American Airlines deal was found by Cheapflights users on 7/1. 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 7/185:57 pmMKE - BOS
1 stop5h 17mAmerican Airlines
Sat 7/267:50 amBOS - MKE
1 stop6h 32mAmerican Airlines
Deal found 7/1$217
This Delta deal was found by Cheapflights users on 7/2. 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 8/267:30 amMKE - MVY
1 stop5h 03mDelta
Sat 8/3011:58 amMVY - MKE
1 stop6h 29mDelta
Deal found 7/2$226
This FlightHub deal was found by Cheapflights users on 7/3. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:48 pmMKE - BDL
1 stop3h 41mSpirit Airlines
Fri 9/126:40 amBDL - MKE
1 stop11h 07mSpirit Airlines
Deal found 7/3$227
This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:51 pmMKE - BOS
1 stop17h 44mSpirit Airlines
Sun 10/1911:34 amBOS - MKE
1 stop24h 27mSpirit Airlines
Deal found 7/2$232
This Delta deal was found by Cheapflights users on 7/3. 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.
Thu 8/74:56 pmMKE - BDL
1 stop5h 52mDelta
Mon 8/117:04 pmBDL - MKE
1 stop5h 45mDelta
Deal found 7/3$237
This Southwest deal was found by Cheapflights users on 7/2. 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.
Thu 8/2112:20 pmMKE - BDL
1 stop6h 40mSouthwest
Mon 8/251:55 pmBDL - MKE
2 stops8h 40mSouthwest
Deal found 7/2$242
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Tue 9/163:47 pmMKE - BDL
1 stop6h 42mAmerican Airlines
Sat 9/2012:09 pmBDL - MKE
1 stop7h 39mAmerican Airlines
Deal found 7/2$259
This Delta deal was found by Cheapflights users on 6/30. 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 7/293:14 pmMKE - ALB
1 stop7h 37mDelta
Tue 8/57:04 pmALB - MKE
1 stop5h 55mDelta
Deal found 6/30$262

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 July 3, 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

Sat 9/27

5:09 pm-8:30 pm

Nonstop2h 21m

Boston Logan Intl

Sat 10/4

2:10 pm-3:38 pm

Nonstop2h 28m

$157

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 8/14

12:20 pm-6:00 pm

1 stop4h 40m

Boston Logan Intl

Mon 8/18

6:40 am-4:15 pm

1 stop10h 35m

$177

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 7/18

5:31 pm-11:16 pm

1 stop4h 45m

Boston Logan Intl

Sat 7/26

8:02 pm-11:54 pm

1 stop4h 52m

$202

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 8/15

7:55 pm-11:19 pm

Nonstop2h 24m

Boston Logan Intl

Mon 8/18

5:20 pm-7:14 pm

Nonstop2h 54m

$207

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 7/18

5:57 pm-12:14 am

1 stop5h 17m

Boston Logan Intl

Sat 7/26

7:50 am-1:22 pm

1 stop6h 32m

$217

MilwaukeeWest Tisbury

MKE - MVY

MKEMVY

Milwaukee-Mitchell

Tue 8/26

7:30 am-1:33 pm

1 stop5h 03m

West Tisbury Martha's Vineyard

Sat 8/30

11:58 am-5:27 pm

1 stop6h 29m

$226

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Mon 9/8

5:48 pm-10:29 pm

1 stop3h 41m

Hartford Bradley Intl

Fri 9/12

6:40 am-4:47 pm

1 stop11h 07m

$231

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 8/14

6:00 am-1:48 pm

1 stop6h 48m

Boston Logan Intl

Mon 8/18

3:37 pm-11:06 pm

1 stop8h 29m

$233

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Thu 8/7

3:14 pm-10:08 pm

1 stop5h 54m

Hartford Bradley Intl

Mon 8/11

7:04 pm-11:49 pm

1 stop5h 45m

$237

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Thu 8/21

2:15 pm-11:25 pm

1 stop8h 10m

Hartford Bradley Intl

Mon 8/25

5:30 am-11:45 am

2 stops7h 15m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 39 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 $218). Flying from Milwaukee to Massachusetts in June is currently the most expensive (average of $306). 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 July 3, 2025.

When flying from Milwaukee to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 July 3, 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
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,861 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,916 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 $89 on American Airlines. Other airlines that offer cheap prices include United Airlines from $94 and Southwest from $99 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 WestJet (92%), JetBlue (75%) or Scandinavian Airlines (73%) 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 $222, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Milwaukee-Mitchell - Boston Logan Intl), you can expect to pay $157 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 $218). Flying from Milwaukee to Massachusetts in June is currently the most expensive (average of $306). 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 6 airlines flying from Milwaukee to Massachusetts

Discover the top 6 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$34Average$258FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$135Average$277FlexibilityNo cancel feeOn-time62%
DeltaCheapest$165Average$385FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$279FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$258FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$186Average$338FlexibilityNo cancel feeOn-time63%

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