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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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
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 September 14, 2025.

Round-trip from

$152
(Southwest)

One-way from

$89
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$277

Good round-trip deal

$166 or less

Good one-way deal

$238 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. 15% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 14, 2025.

This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 11/75:55 pmMKE - BOS
1 stop4h 45mSouthwest
Tue 11/115:45 amBOS - MKE
1 stop4h 45mSouthwest
Deal found 9/12$152
This Southwest deal was found by Cheapflights users on 9/12. 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 10/224:50 pmMKE - BOS
1 stop4h 50mSouthwest
Tue 10/285:00 amBOS - MKE
1 stop7h 45mSouthwest
Deal found 9/12$153
This Southwest deal was found by Cheapflights users on 9/11. 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.
Fri 10/246:00 pmMKE - BOS
1 stop4h 55mSouthwest
Tue 10/285:30 amBOS - MKE
1 stop5h 05mSouthwest
Deal found 9/11$167
This Southwest deal was found by Cheapflights users on 9/12. 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 10/66:10 pmMKE - BOS
1 stop4h 30mSouthwest
Wed 10/85:30 amBOS - MKE
1 stop5h 05mSouthwest
Deal found 9/12$176
This Southwest deal was found by Cheapflights users on 9/13. 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 10/215:45 amMKE - BOS
1 stop5h 05mSouthwest
Wed 10/225:00 amBOS - MKE
1 stop7h 45mSouthwest
Deal found 9/13$177
This Southwest deal was found by Cheapflights users on 9/12. 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.
Fri 10/246:00 pmMKE - BOS
1 stop4h 55mSouthwest
Thu 10/3010:05 amBOS - MKE
1 stop6h 15mSouthwest
Deal found 9/12$183
This JetBlue deal was found by Cheapflights users on 9/12. 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.
Fri 10/174:38 pmMKE - BOS
Nonstop2h 22mJetBlue
Sat 10/252:15 pmBOS - MKE
Nonstop2h 28mJetBlue
Deal found 9/12$187
This Southwest deal was found by Cheapflights users on 9/14. 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 10/224:50 pmMKE - BOS
1 stop4h 50mSouthwest
Sat 10/255:05 amBOS - MKE
1 stop7h 20mSouthwest
Deal found 9/14$192
This Delta deal was found by Cheapflights users on 9/12. 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 11/82:55 pmMKE - BDL
1 stop7h 35mDelta
Tue 11/118:00 amBDL - MKE
1 stop7h 13mDelta
Deal found 9/12$217
This United Airlines deal was found by Cheapflights users on 9/11. 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 11/156:05 amMKE - ALB
1 stop5h 01mUnited Airlines
Sat 11/154:22 pmALB - MKE
1 stop6h 37mUnited Airlines
Deal found 9/11$228
This Delta deal was found by Cheapflights users on 9/12. 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 11/14:49 pmMKE - BDL
1 stop5h 07mDelta
Mon 11/36:00 amBDL - MKE
1 stop8h 09mDelta
Deal found 9/12$230
This United Airlines deal was found by Cheapflights users on 9/12. 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 11/12:45 pmMKE - BDL
2 stops7h 48mUnited Airlines
Mon 11/36:10 pmBDL - MKE
1 stop5h 33mUnited Airlines
Deal found 9/12$235

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 September 14, 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

Fri 10/24

4:38 pm-8:00 pm

Nonstop2h 22m

Boston Logan Intl

Sat 10/25

2:15 pm-3:43 pm

Nonstop2h 28m

$207

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Sat 11/8

2:55 pm-11:30 pm

1 stop7h 35m

Hartford Bradley Intl

Tue 11/11

8:00 am-2:13 pm

1 stop7h 13m

$217

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 10/11

8:20 am-4:22 pm

2 stops7h 02m

Boston Logan Intl

Thu 10/16

6:00 am-10:11 am

1 stop5h 11m

$226

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 10/3

1:20 pm-9:35 pm

1 stop7h 15m

Boston Logan Intl

Tue 10/7

5:00 am-11:45 am

1 stop7h 45m

$228

MilwaukeeAlbany

MKE - ALB

MKEALB

Milwaukee-Mitchell

Sat 11/15

6:05 am-12:06 pm

1 stop5h 01m

Albany Intl

Sat 11/15

4:22 pm-9:59 pm

1 stop6h 37m

$228

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Sat 11/1

4:49 pm-10:56 pm

1 stop5h 07m

Hartford Bradley Intl

Mon 11/3

6:00 am-1:09 pm

1 stop8h 09m

$230

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Sat 11/8

12:06 pm-6:35 pm

1 stop5h 29m

Hartford Bradley Intl

Mon 11/10

7:06 pm-11:56 pm

1 stop5h 50m

$230

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 10/31

2:35 pm-8:40 pm

1 stop5h 05m

Boston Logan Intl

Mon 11/3

5:35 pm-9:45 pm

1 stop5h 10m

$236

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Fri 10/24

4:49 pm-11:14 pm

1 stop5h 25m

Hartford Bradley Intl

Wed 10/29

6:10 am-10:11 am

1 stop5h 01m

$244

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Tue 9/30

4:00 pm-11:59 pm

1 stop6h 59m

Hartford Bradley Intl

Fri 10/3

5:08 pm-11:48 pm

1 stop7h 40m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 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 July is currently the most expensive (average of $311). 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 September 14, 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.

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 September 14, 2025.

The most flights from MKE to USMA are scheduled on a Sunday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (4 on average).

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 September 14, 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
4,245 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,956 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,912 reviews
Southwest
8.0
Very good
4,245 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 6 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 JetBlue, Delta, and United Airlines fly from Milwaukee to Massachusetts in about 2h 22m. The time it takes to get you to your destination can typically vary by up to 5h 13m. 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 $89 on United Airlines. Other airlines that offer cheap prices include JetBlue from $94 and Southwest from $100 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 Air France (88%), Delta (79%) or Republic Airways (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 $281, 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 $152 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 July is currently the most expensive (average of $311). 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$119Average$280FlexibilityNo cancel feeOn-time62%
DeltaCheapest$160Average$383FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$164Average$267FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$184Average$272FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$306FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$186Average$289FlexibilityNo cancel feeOn-time63%

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