HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 7/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jul 21 — Jul 281
Mon 7/21
Mon 7/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Milwaukee to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 16, 2025.

Round-trip from

$157
(JetBlue)

One-way from

$89
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$282

Good round-trip deal

$153 or less

Good one-way deal

$108 or less
From Milwaukee-Mitchell to Massachusetts
Search Deals
One-way flight from Milwaukee-Mitchell to Massachusetts
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
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

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 16, 2025.

This JetBlue deal was found by Cheapflights users on 7/15. 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 10/14:29 pmMKE - BOS
Nonstop2h 21mJetBlue
Tue 10/72:05 pmBOS - MKE
Nonstop2h 28mJetBlue
Deal found 7/15$157
This American Airlines deal was found by Cheapflights users on 7/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1610:34 amMKE - BOS
1 stop5h 12mAmerican Airlines
Tue 9/167:25 pmBOS - MKE
1 stop5h 05mAmerican Airlines
Deal found 7/16$171
This Southwest deal was found by Cheapflights users on 7/14. 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 8/137:35 amMKE - BOS
2 stops8h 30mSouthwest
Wed 8/206:05 pmBOS - MKE
1 stop5h 00mSouthwest
Deal found 7/14$182
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/267:00 amMKE - BOS
2 stops6h 13mUnited Airlines
Sun 8/317:45 amBOS - MKE
1 stop4h 45mUnited Airlines
Deal found 7/14$209
This FlightHub deal was found by Cheapflights users on 7/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/83:06 pmMKE - BDL
1 stop6h 41mSpirit Airlines
Fri 9/126:10 amBDL - MKE
1 stop8h 54mSpirit Airlines
Deal found 7/14$217
This FlightHub deal was found by Cheapflights users on 7/15. 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 8/216:00 amMKE - BOS
1 stop6h 48mSpirit Airlines
Mon 8/256:30 amBOS - MKE
1 stop11h 09mSpirit Airlines
Deal found 7/15$229
This Delta deal was found by Cheapflights users on 7/15. 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 8/302:13 pmMVY - MKE
1 stop7h 11mDelta
Deal found 7/15$236
This Delta deal was found by Cheapflights users on 7/15. 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 8/56:45 amMKE - BDL
1 stop5h 36mDelta
Sat 8/166:41 pmBDL - MKE
1 stop3h 52mDelta
Deal found 7/15$237
This Delta deal was found by Cheapflights users on 7/15. 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 8/196:32 pmMKE - ALB
1 stop3h 49mDelta
Sat 8/236:50 pmALB - MKE
1 stop5h 39mDelta
Deal found 7/15$237
This Delta deal was found by Cheapflights users on 7/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:55 pmMKE - BOS
Nonstop2h 23mDelta
Sat 9/65:30 pmBOS - MKE
1 stop5h 03mDelta
Deal found 7/13$237
This Southwest deal was found by Cheapflights users on 7/15. 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 8/57:00 amMKE - BDL
1 stop4h 05mSouthwest
Tue 8/194:00 pmBDL - MKE
2 stops7h 25mSouthwest
Deal found 7/15$242
This United Airlines deal was found by Cheapflights users on 7/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:00 amMKE - ALB
1 stop7h 05mUnited Airlines
Wed 9/36:00 amALB - MKE
2 stops6h 30mUnited Airlines
Deal found 7/14$242

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 16, 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

Wed 10/1

4:29 pm-7:50 pm

Nonstop2h 21m

Boston Logan Intl

Tue 10/7

2:05 pm-3:33 pm

Nonstop2h 28m

$157

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 9/16

10:34 am-4:46 pm

1 stop5h 12m

Boston Logan Intl

Tue 9/16

7:25 pm-11:30 pm

1 stop5h 05m

$171

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 8/13

7:35 am-1:45 pm

1 stop5h 10m

Boston Logan Intl

Wed 8/20

7:35 am-11:30 am

1 stop4h 55m

$177

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 8/26

7:00 am-2:13 pm

2 stops6h 13m

Boston Logan Intl

Sun 8/31

7:45 am-11:30 am

1 stop4h 45m

$209

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Mon 9/8

3:06 pm-10:47 pm

1 stop6h 41m

Hartford Bradley Intl

Fri 9/12

6:10 am-2:04 pm

1 stop8h 54m

$217

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 8/21

6:00 am-1:48 pm

1 stop6h 48m

Boston Logan Intl

Mon 8/25

6:30 am-4:39 pm

1 stop11h 09m

$229

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

2:13 pm-8:24 pm

1 stop7h 11m

$236

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Tue 8/5

7:00 am-12:05 pm

1 stop4h 05m

Hartford Bradley Intl

Tue 8/19

4:00 pm-9:50 pm

1 stop6h 50m

$237

MilwaukeeAlbany

MKE - ALB

MKEALB

Milwaukee-Mitchell

Tue 8/19

6:32 pm-11:21 pm

1 stop3h 49m

Albany Intl

Sat 8/23

6:50 pm-11:29 pm

1 stop5h 39m

$237

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 8/26

6:55 pm-10:18 pm

Nonstop2h 23m

Boston Logan Intl

Thu 9/4

5:15 am-8:43 am

1 stop4h 28m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/14

Showing 1-10 of 39 results
1
2
3
4

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 $307). 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 16, 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 16, 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
4,241 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
7,957 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
8,863 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
2,909 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
4,241 reviews

Food

7.0

Crew

8.6

Entertainment

7.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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 United Airlines. Other airlines that offer cheap prices include American Airlines from $94 and JetBlue 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 JetBlue (74%), Scandinavian Airlines (73%) or Delta (68%) 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 $196, 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 July is currently the most expensive (average of $307). 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Milwaukee to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to Seattle flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Boston flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Denver flights
Minneapolis to Las Vegas flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Minneapolis to LaGuardia flights
Minneapolis to Seattle flights
O'Hare Intl to San Diego flights
Minneapolis to Denver flights
O'Hare Intl to Portland flights
O'Hare Intl to Ontario flights
Minneapolis to Dallas/Fort Worth flights
Minneapolis to Boston flights
Minneapolis to Orlando flights
Milwaukee to Seattle flights
O'Hare Intl to Philadelphia flights
Minneapolis to Newark flights
O'Hare Intl to Honolulu flights
Minneapolis to John F Kennedy Intl flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Reagan-National flights
Minneapolis to Sky Harbor Intl flights
O'Hare Intl to Nashville flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Dulles Intl flights
Minneapolis to O'Hare Intl flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Burbank flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Atlanta flights
O'Hare Intl to Hobby flights
Minneapolis to Cleveland flights
Milwaukee to LaGuardia flights
Minneapolis to Hobby flights
O'Hare Intl to Fort Myers flights
Minneapolis to Miami flights
Minneapolis to George Bush Intcntl flights
Minneapolis to Midway flights

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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$79Average$267FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$130Average$281FlexibilityNo cancel feeOn-time62%
DeltaCheapest$159Average$381FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$276FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$260FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$186Average$315FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.