$104+ Cheap flights from Milwaukee (MKE) to Massachusetts
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Nov 25 — Dec 21
Round-trip
1 adult, Economy
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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
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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
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Cheapest flights from Milwaukee to MassachusettsExplore 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 October 26, 2026.
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 October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/22. 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 11/2611:20 am -
1 stop4h 45m
Tue 12/295:35 am -
1 stop4h 55m
Deal found 10/22![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 10/22. 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 11/186:20 am -
2 stops7h 10m
Mon 11/235:10 am -
1 stop5h 30m
Deal found 10/22![Southwest logo]()
$294
This American Airlines deal was found by Cheapflights users on 10/21. 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 12/2510:47 am -
1 stop6h 16m
Wed 12/306:53 pm -
1 stop6h 06m
Deal found 10/21![American Airlines logo]()
$297
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:00 am -
1 stop5h 20m
Sun 12/65:56 pm -
1 stop5h 41m
Deal found 10/26![American Airlines logo]()
$298
This Southwest deal was found by Cheapflights users on 10/23. 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 11/188:00 am -
2 stops8h 10m
Thu 11/195:10 am -
1 stop5h 30m
Deal found 10/23![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 10/23. 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.
Mon 11/95:50 pm -
1 stop4h 35m
Tue 11/105:30 am -
1 stop7h 30m
Deal found 10/23![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sat 11/214:40 pm -
1 stop6h 30m
Sun 11/225:10 am -
1 stop5h 30m
Deal found 10/22![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 10/23. 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.
Thu 12/106:20 am -
2 stops7h 10m
Sun 12/135:10 am -
1 stop5h 30m
Deal found 10/23![Southwest logo]()
$321
This Southwest deal was found by Cheapflights users on 10/22. 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 11/135:50 pm -
1 stop4h 35m
Sun 11/155:10 am -
1 stop5h 30m
Deal found 10/22![Southwest logo]()
$335
Best flights from Milwaukee to MassachusettsDiscover carefully curated flight deals from Milwaukee to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
Discover carefully curated flight deals from Milwaukee to Massachusetts that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 26, 2026.
This Southwest deal was found by Cheapflights users on 10/23. 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.
Mon 11/95:50 pm -
1 stop4h 35m
Tue 11/105:30 am -
1 stop7h 30m
Deal found 10/23![Southwest logo]()
$307
This Delta deal was found by Cheapflights users on 10/21. 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 12/312:10 pm -
Nonstop2h 27m
Sun 1/35:30 am -
1 stop4h 27m
Deal found 10/21![Delta logo]()
$429
This Southwest deal was found by Cheapflights users on 10/22. 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 11/56:25 pm -
1 stop4h 30m
Mon 11/93:30 pm -
2 stops9h 05m
Deal found 10/22![Southwest logo]()
$376
This Southwest deal was found by Cheapflights users on 10/22. 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 11/198:00 am -
2 stops8h 10m
Fri 11/203:30 pm -
2 stops9h 05m
Deal found 10/22![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 10/21. 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 12/293:57 pm -
1 stop6h 09m
Sat 1/211:35 am -
Nonstop2h 54m
Deal found 10/21![Delta logo]()
$429
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sun 12/205:45 am -
2 stops7h 00m
Mon 12/287:40 pm -
1 stop5h 00m
Deal found 10/21![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
Nonstop2h 31m
Sun 1/108:25 pm -
Nonstop2h 55m
Deal found 10/25![Delta logo]()
$439
This Southwest deal was found by Cheapflights users on 10/21. 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 12/235:45 am -
2 stops7h 05m
Thu 12/315:10 am -
1 stop5h 30m
Deal found 10/21![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 10/24. 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.
Mon 11/237:35 am -
Nonstop2h 26m
Fri 11/279:30 am -
Nonstop2h 52m
Deal found 10/24![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/207:40 am -
Nonstop2h 35m
Thu 1/288:25 pm -
Nonstop2h 55m
Deal found 10/25![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 10/24. 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.
Thu 12/37:35 am -
Nonstop2h 27m
Mon 12/76:30 pm -
Nonstop2h 58m
Deal found 10/24![Delta logo]()
$439
Last-minute flights from Milwaukee to MassachusettsDiscover last-minute flight deals from Milwaukee to Massachusetts. Data last updated October 26, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Massachusetts. Data last updated October 26, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/23. 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.
Fri 11/64:50 pm -
1 stop4h 15m
Mon 11/97:45 pm -
1 stop4h 50m
Deal found 10/23![Southwest logo]()
$339
This Southwest deal was found by Cheapflights users on 10/23. 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.
Mon 11/95:50 pm -
1 stop4h 35m
Tue 11/105:30 am -
1 stop7h 30m
Deal found 10/23![Southwest logo]()
$307
This Southwest deal was found by Cheapflights users on 10/22. 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 11/135:50 pm -
1 stop4h 35m
Sun 11/155:10 am -
1 stop5h 30m
Deal found 10/22![Southwest logo]()
$335
This Southwest deal was found by Cheapflights users on 10/22. 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 11/186:20 am -
2 stops7h 10m
Mon 11/235:10 am -
1 stop5h 30m
Deal found 10/22![Southwest logo]()
$294
This Southwest deal was found by Cheapflights users on 10/23. 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 11/188:00 am -
2 stops8h 10m
Thu 11/195:10 am -
1 stop5h 30m
Deal found 10/23![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 10/22. 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 11/198:00 am -
2 stops8h 10m
Fri 11/207:45 pm -
1 stop4h 50m
Deal found 10/22![Southwest logo]()
$340
This Southwest deal was found by Cheapflights users on 10/22. 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.
Sat 11/214:40 pm -
1 stop6h 30m
Sun 11/225:10 am -
1 stop5h 30m
Deal found 10/22![Southwest logo]()
$309
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:08 am -
1 stop6h 07m
Wed 12/22:50 pm -
1 stop6h 33m
Deal found 10/26![American Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 10/22. 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 11/2611:20 am -
1 stop4h 45m
Tue 12/295:35 am -
1 stop4h 55m
Deal found 10/22![Southwest logo]()
$284
One-way flights from Milwaukee to MassachusettsSearch for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
Search for one-way flight options from Milwaukee to Massachusetts. Find affordable one-way fares based on user searches. Data last updated October 26, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/256:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$104
This CheapOair deal was found by Cheapflights users on 10/25. 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.
Tue 11/246:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 10/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$124
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/212:30 pm -
1 stop8h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 10/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$144
This Southwest deal was found by Cheapflights users on 10/22. 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 12/18:00 am -
2 stops8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$147
This American Airlines deal was found by Cheapflights users on 10/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/256:00 am -
1 stop6h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![American Airlines logo]()
$149
This CheapOair deal was found by Cheapflights users on 10/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/185:47 pm -
1 stop14h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Frontier logo]()
$151
This Southwest deal was found by Cheapflights users on 10/22. 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 11/198:00 am -
2 stops8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$153
This Southwest deal was found by Cheapflights users on 10/23. 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.
Mon 11/95:50 pm -
1 stop4h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Southwest logo]()
$154
This Southwest deal was found by Cheapflights users on 10/22. 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 11/116:35 am -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Southwest logo]()
$159
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 October 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $284 (Southwest) |
One-way from | $104 (Cheapflightsfares) |
Popular in | November |
Cheapest in | May |
Average price | $391 |
Good round-trip deal | $399 or less |
Good one-way deal | $218 or less |
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 7,457,451 searches. Data last updated October 26, 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
Cheapest round-trip
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 11/11
6:35 am-2:30 pm
1 stop6h 55m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Mon 11/9
4:05 pm-11:55 pm
2 stops6h 50m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$171
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 12/6
7:55 am-3:40 pm
2 stops6h 45m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$173
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Thu 11/5
6:55 am-2:30 pm
1 stop6h 35m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$186
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Tue 11/10
7:35 am-11:01 am
Nonstop2h 26m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$204
Quickest round-trip
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Tue 1/5
7:00 am-10:23 am
Nonstop2h 23m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$229
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 1/24
7:00 am-10:23 am
Nonstop2h 23m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$229
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Wed 12/2
7:35 am-11:02 am
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$229
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Mon 12/28
5:45 am-1:50 pm
2 stops7h 05m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$235
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sun 1/3
6:40 pm-11:59 pm
1 stop4h 19m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$239
Showing 1-10 of 23 resultsSorted by cheapest first
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.
MKE-BOS
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
MKE-USMA
MKE-BOS
What is the cheapest month to book a flight from Milwaukee to Massachusetts?
Currently, May is the cheapest month in which you can book a flight from Milwaukee to Massachusetts (average of $235). Flying from Milwaukee to Massachusetts in November is currently the most expensive (average of $435). 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 October 26, 2026.
A simple way to save on the total cost of your ticket is to fly from Milwaukee to Massachusetts in the afternoon. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight at noon.
How much does it cost to fly round-trip from Milwaukee to Massachusetts?
Airfare is below average for this route at the moment.
Milwaukee to Massachusetts flights typically cost between $336 and $500 in November.The cheapest round-trip price found within the last 5 days was $284 on Southwest (Nov 26-Dec 29).
How far ahead should I book a flight from Milwaukee to Massachusetts?
To ensure you get the cheapest price possible for a flight from Milwaukee to Massachusetts, you should look to book at least 82 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 October 24, 2026.
Travelers seeking maximum savings on their Milwaukee to Massachusetts flight should consider departing on Saturday evenings when fares are most often at their lowest. Monday 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 October 26, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andUnited 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.
Entertainment
7.4
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.4
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
7.9
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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Milwaukee and Massachusetts flights
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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 7,457,451 searches. Data last updated October 26, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$385 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$251 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$343 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$329 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$377 | FlexibilityNo cancel fee | On-time63% |