$104+ Cheap flights from Milwaukee to Boston (MKE - BOS)
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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Nov 22 — Nov 291
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Boston 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.Cheapflights Tip: The best prices from Milwaukee-Mitchell to Boston Logan Intl are usually found in May or June, booked 83 days in advance, depart on a Saturday or Wednesday and return on a Saturday
Cheap flight deals from Milwaukee to Boston
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Cheapest flights from Milwaukee to BostonExplore the most affordable flight options available from Milwaukee to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
Explore the most affordable flight options available from Milwaukee to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2026.
This American Airlines deal was found by Cheapflights users on 10/20. 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 10/20![American Airlines logo]()
$277
This Frontier deal was found by Cheapflights users on 10/20. 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.
Thu 11/1910:15 am -
1 stop22h 56m
Sun 11/2211:06 am -
1 stop7h 20m
Deal found 10/20![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 10/19. 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 11/196:35 am -
1 stop4h 45m
Mon 11/234:20 pm -
1 stop6h 55m
Deal found 10/19![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 10/18. 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 11/168:00 am -
1 stop7h 50m
Mon 11/235:10 am -
1 stop5h 30m
Deal found 10/18![Southwest logo]()
$289
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 12/257:00 am -
1 stop5h 51m
Thu 12/3112:16 pm -
1 stop6h 04m
Deal found 10/21![American Airlines logo]()
$297
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.
Thu 11/125:30 am -
2 stops8h 00m
Mon 11/165:20 am -
1 stop5h 20m
Deal found 10/21![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 10/20. 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 11/94:05 pm -
1 stop6h 40m
Mon 11/165:10 am -
1 stop5h 30m
Deal found 10/20![Southwest logo]()
$301
This Southwest deal was found by Cheapflights users on 10/20. 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 11/215:25 pm -
1 stop6h 25m
Fri 11/275:10 am -
1 stop5h 30m
Deal found 10/20![Southwest logo]()
$309
This Southwest deal was found by Cheapflights users on 10/20. 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 11/136:25 pm -
1 stop4h 30m
Tue 11/175:00 am -
1 stop10h 05m
Deal found 10/20![Southwest logo]()
$315
Best flights from Milwaukee to BostonDiscover carefully curated flight deals from Milwaukee to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
Discover carefully curated flight deals from Milwaukee to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 23, 2026.
This Southwest deal was found by Cheapflights users on 10/19. 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 11/215:25 pm -
1 stop6h 25m
Thu 12/103:30 pm -
2 stops7h 45m
Deal found 10/19![Southwest logo]()
$289
This Delta deal was found by Cheapflights users on 10/18. 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 11/256:45 pm -
1 stop4h 09m
Fri 11/279:30 am -
Nonstop2h 52m
Deal found 10/18![Delta logo]()
$429
This Southwest deal was found by Cheapflights users on 10/20. 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 11/94:50 pm -
1 stop4h 15m
Mon 11/163:30 pm -
2 stops7h 50m
Deal found 10/20![Southwest logo]()
$306
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 11/64:50 pm -
1 stop4h 15m
Mon 11/93:30 pm -
2 stops9h 05m
Deal found 10/22![Southwest logo]()
$376
This Delta deal was found by Cheapflights users on 10/18. 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 12/47:35 am -
Nonstop2h 27m
Mon 12/74:59 pm -
1 stop4h 23m
Deal found 10/18![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 10/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/207:00 am -
Nonstop2h 23m
Thu 1/287:40 pm -
Nonstop2h 53m
Deal found 10/22![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 10/18. 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 11/238:10 am -
1 stop5h 28m
Fri 11/275:30 am -
1 stop4h 20m
Deal found 10/18![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 10/18. 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 12/301:10 pm -
1 stop6h 42m
Fri 1/110:38 am -
Nonstop2h 52m
Deal found 10/18![Delta logo]()
$458
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 11/56:55 am -
1 stop6h 35m
Mon 11/99:00 am -
Nonstop2h 55m
Deal found 10/22![Southwest logo]()
$439
Last-minute flights from Milwaukee to BostonDiscover last-minute flight deals from Milwaukee to Boston. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Boston. Data last updated October 23, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/20. 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 11/94:05 pm -
1 stop6h 40m
Mon 11/165:10 am -
1 stop5h 30m
Deal found 10/20![Southwest logo]()
$301
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.
Thu 11/125:30 am -
2 stops8h 00m
Mon 11/165:20 am -
1 stop5h 20m
Deal found 10/21![Southwest logo]()
$300
This Southwest deal was found by Cheapflights users on 10/20. 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 11/136:25 pm -
1 stop4h 30m
Tue 11/175:00 am -
1 stop10h 05m
Deal found 10/20![Southwest logo]()
$315
This Southwest deal was found by Cheapflights users on 10/19. 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 11/168:00 am -
1 stop7h 50m
Mon 11/234:20 pm -
1 stop6h 55m
Deal found 10/19![Southwest logo]()
$289
This Frontier deal was found by Cheapflights users on 10/20. 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.
Thu 11/1910:15 am -
1 stop22h 56m
Sun 11/2211:06 am -
1 stop7h 20m
Deal found 10/20![Frontier logo]()
$281
This Southwest deal was found by Cheapflights users on 10/19. 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 11/196:35 am -
1 stop4h 45m
Mon 11/234:20 pm -
1 stop6h 55m
Deal found 10/19![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 10/20. 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 11/215:25 pm -
1 stop6h 25m
Fri 11/275:10 am -
1 stop5h 30m
Deal found 10/20![Southwest logo]()
$309
One-way flights from Milwaukee to BostonSearch for one-way flight options from Milwaukee to Boston. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
Search for one-way flight options from Milwaukee to Boston. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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.
Tue 11/246:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$104
This CheapOair deal was found by Cheapflights users on 10/20. 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.
Wed 11/256:11 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![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.
Tue 12/12:55 pm -
1 stop5h 26m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![American Airlines logo]()
$129
This Southwest deal was found by Cheapflights users on 10/20. 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 12/1012:45 pm -
1 stop10h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Southwest logo]()
$142
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 10/19. 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 11/166:35 am -
1 stop6h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Southwest logo]()
$147
This American Airlines deal was found by Cheapflights users on 10/20. 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.
Sun 12/62:51 pm -
1 stop7h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![American Airlines logo]()
$149
Find flight deals from Milwaukee to Boston
Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $277 (American Airlines) |
One-way from | $104 (Cheapflightsfares) |
Popular in | November |
Cheapest in | May |
Average price | $390 |
Good round-trip deal | $399 or less |
Good one-way deal | $208 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Boston 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 23, 2026.
Use the filters below to find and compare flights from Milwaukee to Boston 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
Thu 1/7
7:45 am-5:55 pm
2 stops9h 10m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$147
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
Sat 11/7
5:45 am-10:55 am
1 stop4h 10m
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
Sun 11/8
5:30 am-11:10 am
1 stop4h 40m
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
Sat 12/5
9:40 am-1:05 pm
Nonstop2h 25m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
Quickest round-trip
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Mon 11/23
2:30 pm-5:53 pm
Nonstop2h 23m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Mon 12/7
7:35 am-11:02 am
Nonstop2h 27m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$219
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Fri 11/27
5:30 am-11:10 am
1 stop4h 40m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$220
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Fri 11/20
6:25 pm-11:55 pm
1 stop4h 30m
Boston Logan Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$220
MilwaukeeBoston
MKE Milwaukee-Mitchell - BOS Boston Logan Intl
MKEBOS
Milwaukee-Mitchell
Sat 11/21
5:25 pm-12:50 am
1 stop6h 25m
Boston Logan Intl
Thu 12/10
3:30 pm-10:15 pm
2 stops7h 45m
$289
Showing 1-10 of 20 resultsSorted by cheapest first
Compare providers for flights from Milwaukee to Boston
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Milwaukee to Boston in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on Milwaukee-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Boston flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Milwaukee-Boston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Milwaukee-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Milwaukee to Boston
Have a flexible travel schedule? Discover the best time to fly to Boston 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 Boston
Prices
More
How far ahead should I book a flight from Milwaukee to Boston?
The price you pay for your flight from Milwaukee to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 82 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Milwaukee to Boston?
Currently, May is the cheapest month in which you can book a flight from Milwaukee to Boston (average of $235). Flying from Milwaukee to Boston 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 BOS?
Find hourly flight availability from Milwaukee to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2026.
A simple way to save on the total cost of your ticket is to fly from Milwaukee to Boston in the afternoon. If you’re flexible enough to do this you can expect to save up to 37% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Milwaukee to Boston?
Use this chart to determine the cheapest time to fly round-trip from Milwaukee to Boston. Price data was last updated on October 17, 2026.
Travelers seeking maximum savings on their Milwaukee to Boston 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.
What’s the top layover airport for flights from Milwaukee to Boston?
Share of 1-stop round-trip flights from Milwaukee to Boston chosen by Cheapflights users in the past 12 months, using the same layover each way.
Chicago (ORD) – chosen by Cheapflights users on 50% of 1-stop itineraries from Milwaukee to Boston on Cheapflights.
What’s the cheapest layover airport for flights from Milwaukee to Boston?
Average round-trip fare for 1-stop flights from Milwaukee to Boston, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Chicago (ORD) is the most affordable 1-stop option, with an average round-trip price of $186.
What’s the fastest layover option from Milwaukee to Boston?
Shortest average travel time for 1-stop one-way flights from Milwaukee to Boston, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Philadelphia (PHL) have the shortest average one-way travel time for 1-stop routes: 4h 54m.
Which airport typically offers the quickest layover for flights from Milwaukee to Boston?
Average layover duration for 1-stop one-way flights from Milwaukee to Boston, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Philadelphia (PHL) offer the fastest connection on this route, with an average layover time of 1h 10m.
Reviews of airlines servicing Boston
Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated October 23, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Milwaukee to Boston have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Boarding
8.1
Entertainment
7.4
Comfort
8.0
Overall
7.9
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Fitchburg
Londonderry
York Beach
Revere
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
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Top 5 airlines flying from Milwaukee to Boston
Discover the top 5 airlines that operate flights from Milwaukee to Boston. 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 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$113 | Average$382 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$251 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$337 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$186 | Average$332 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$231 | Average$377 | FlexibilityNo cancel fee | On-time63% |