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$104+ Cheap flights from Milwaukee to Boston (MKE - BOS)

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
nov. 26 — déc. 31
mer. 11/26
mer. 12/3
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Boston Logan Intl are usually found in September or August, booked 63 days in advance, depart on a Saturday or Thursday and return on a Wednesday

Cheap 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 octobre 27, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Southwest)

One-way from

$104
(Southwest)

Popular in

December

Cheapest in

September

Average price

$282

Good round-trip deal

$258 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
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From Milwaukee-Mitchell to Boston Logan Intl
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One-way flight from Milwaukee-Mitchell to Boston Logan Intl
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Highest demand for flights based on searches. 17% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Milwaukee-Mitchell to Boston Logan Intl.
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Price to beat on a one-way flight from Milwaukee-Mitchell to Boston Logan Intl.
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Find flight deals from Milwaukee to Boston

Cheapest flights from Milwaukee to Boston
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 octobre 27, 2025.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/155:15 amMKE - BOS
1 stop9h 35mSouthwest
mar. 11/187:20 amBOS - MKE
1 stop5h 20mSouthwest
Deal found 10/26$207
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/85:15 amMKE - BOS
1 stop9h 35mSouthwest
sam. 11/1512:45 pmBOS - MKE
1 stop7h 10mSouthwest
Deal found 10/25$237
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 12/125:50 amMKE - BOS
1 stop4h 35mSouthwest
ven. 12/127:20 pmBOS - MKE
1 stop5h 10mSouthwest
Deal found 10/26$247
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/86:00 amMKE - BOS
1 stop4h 45mSouthwest
mar. 12/91:35 pmBOS - MKE
2 stops8h 55mSouthwest
Deal found 10/26$252
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.
ven. 11/143:49 pmMKE - BOS
1 stop7h 27mAmerican Airlines
dim. 11/166:00 amBOS - MKE
1 stop7h 07mAmerican Airlines
Deal found 10/26$257
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/810:34 amMKE - BOS
1 stop22h 27mSpirit Airlines
sam. 12/138:11 pmBOS - MKE
1 stop14h 28mSpirit Airlines
Deal found 10/24$260
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/82:10 pmMKE - BOS
1 stop6h 45mSouthwest
dim. 11/166:50 amBOS - MKE
1 stop5h 15mSouthwest
Deal found 10/25$267
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/810:34 amMKE - BOS
1 stop22h 27mSpirit Airlines
dim. 12/148:11 pmBOS - MKE
1 stop14h 28mSpirit Airlines
Deal found 10/24$270
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/1011:30 amMKE - BOS
2 stops8h 35mSouthwest
dim. 12/145:00 amBOS - MKE
1 stop7h 15mSouthwest
Deal found 10/24$277
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 12/410:34 amMKE - BOS
2 stops19h 59mMultiple Airlines
dim. 12/712:57 pmBOS - MKE
1 stop21h 42mMultiple Airlines
Deal found 10/25$280
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 11/85:45 amMKE - BOS
2 stops9h 20mSouthwest
mar. 11/115:45 amBOS - MKE
1 stop4h 45mSouthwest
Deal found 10/25$282

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 2,558,603 searches. Data last updated octobre 27, 2025.
Use the filters below to find and compare flights from Milwaukee to Boston that are best for you.

Fly from

Milwaukee

Fly to

Boston

Route

Depart

Return

Price

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

jeu. 12/25

2:40 pm-10:15 pm

1 stop6h 35m

Boston Logan Intl

mar. 12/30

8:10 pm-11:45 pm

1 stop4h 35m

$247

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

lun. 12/8

4:05 pm-10:15 pm

1 stop5h 10m

Boston Logan Intl

mar. 12/9

5:35 pm-9:45 pm

1 stop5h 10m

$247

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

ven. 11/14

5:10 pm-11:15 pm

1 stop5h 05m

Boston Logan Intl

sam. 11/15

5:55 am-5:55 pm

2 stops13h 00m

$282

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

ven. 12/12

5:50 am-11:25 am

1 stop4h 35m

Boston Logan Intl

ven. 12/12

3:25 pm-11:25 pm

2 stops9h 00m

$302

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

mer. 12/10

7:00 am-10:16 am

Nonstop2h 16m

Boston Logan Intl

lun. 12/15

7:40 pm-9:26 pm

Nonstop2h 46m

$319

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

mer. 12/10

7:00 am-10:16 am

Nonstop2h 16m

Boston Logan Intl

mar. 12/16

7:40 pm-9:26 pm

Nonstop2h 46m

$319

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

jeu. 12/11

7:00 am-10:16 am

Nonstop2h 16m

Boston Logan Intl

mar. 12/16

7:40 pm-9:26 pm

Nonstop2h 46m

$319

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

jeu. 12/4

7:00 am-10:16 am

Nonstop2h 16m

Boston Logan Intl

dim. 12/7

7:40 pm-9:26 pm

Nonstop2h 46m

$319

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

ven. 12/5

7:00 am-10:16 am

Nonstop2h 16m

Boston Logan Intl

dim. 12/7

7:40 pm-9:26 pm

Nonstop2h 46m

$319

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

mar. 12/9

7:00 am-10:16 am

Nonstop2h 16m

Boston Logan Intl

sam. 12/13

3:34 pm-5:16 pm

Nonstop2h 42m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 22 results
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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.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • 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.
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

How far ahead should I book a flight from Milwaukee to Boston?

Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to Boston. Price data was last updated on October 24, 2025.

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 63 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, November is the cheapest month in which you can book a flight from Milwaukee to Boston (average of $71). Flying from Milwaukee to Boston in February is currently the most expensive (average of $137). 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 octobre 27, 2025.

A simple way to save on the total cost of your ticket is to fly from Milwaukee to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 49% 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 26, 2025.

Travelers seeking maximum savings on their Milwaukee to Boston flight should consider departing on Monday evenings when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 octobre 27, 2025.
See what other customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
7.9
Good
7,996 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
8,997 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
11,033 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
2,907 reviews
Southwest
8.0
Very good
4,236 reviews

Entertainment

7.5

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

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 Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airports do I use to fly from Milwaukee to Boston?

    You will need to book a flight from Milwaukee-Mitchell to Boston Logan Intl if you want to fly from Milwaukee to Boston. At least 6 different airlines have flights from Milwaukee-Mitchell (MKE) to Logan Intl (BOS) on a regular basis. There are 4 flights to Boston from the Milwaukee airport per day. If you manage to book one that is nonstop, then you can expect the flight time from MKE to BOS to be around 2h 16m.

  • How popular is this Milwaukee to Boston flight route?

    This flight path from Milwaukee-Mitchell to Boston Logan Intl was viewed by 7 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 Boston?

    Southwest and Delta can get you from Milwaukee to Boston in just under 2h 16m. Your travel time can differ by up to 4h 19m. Airlines will cover a distance of 857 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Milwaukee to Boston round-trip?

    Flying on JetBlue is currently your cheapest option to Boston, with prices starting at $114. Additional round-trip tickets that might be worth considering are offered by Delta and Spirit Airlines, with the lowest prices starting at $153 and $164, respectively. Users have found that JetBlue is 64% cheaper than the other options available to this destination.

  • What are the most reliable airlines from Milwaukee to Boston?

    No one likes to see their flight delayed. When booking a flight from Milwaukee to Boston consider choosing Delta (70%), Republic Airways (70%) or KLM (60%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Milwaukee to Boston?

    The cheapest flight price from Milwaukee to Boston is $133. On average you can expect to pay $912. The most popular route, (Milwaukee-Mitchell - Boston Logan Intl), can usually be booked for $213.

  • Can I find deals for flights from Milwaukee to Boston that include hotel bookings?

    Yes. In addition to deals on Milwaukee to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Milwaukee to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Milwaukee to Boston.

  • Can I find deals for business class flights from Milwaukee to Boston?

    Yes. Cheapflights offers flight deals from Milwaukee to Boston 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 Boston?

    Currently, November is the cheapest month in which you can book a flight from Milwaukee to Boston (average of $71). Flying from Milwaukee to Boston in February is currently the most expensive (average of $137). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Alternative routes for Milwaukee to Boston

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Top 6 airlines flying from Milwaukee to Boston

Discover the top 6 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 2,558,603 searches. Data last updated octobre 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$276FlexibilityNo cancel feeOn-time62%
DeltaCheapest$152Average$379FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$164Average$258FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$266FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$177Average$281FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$321FlexibilityNo cancel feeOn-time69%

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