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$76+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Find cheap flights from Milwaukee to Boston with Cheapflights

1. Tell us where you want to go

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3. Compare prices and book

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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Boston Logan Intl are usually found in September or May, booked 62 days in advance, depart on a Friday or Wednesday and return on a Saturday

Cheap 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 April 23, 2026.

This Expedia deal was found by Cheapflights users on 4/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1112:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Wed 5/136:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Deal found 4/20$140
This Expedia deal was found by Cheapflights users on 4/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2012:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Wed 5/276:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Deal found 4/20$160
This Frontier deal was found by Cheapflights users on 4/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/812:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Mon 5/116:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Deal found 4/19$161
This Priceline deal was found by Cheapflights users on 4/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:58 pm
MKE
-
BOS
Nonstop2h 17m
Multiple Airlines
Wed 5/136:00 am
BOS
-
MKE
1 stop6h 14m
Multiple Airlines
Deal found 4/21$164
This CheapOair deal was found by Cheapflights users on 4/20. 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.
Sat 5/95:17 pm
MKE
-
BOS
Nonstop2h 15m
Multiple Airlines
Wed 5/136:00 am
BOS
-
MKE
1 stop6h 14m
Multiple Airlines
Deal found 4/20$169
This CheapOair deal was found by Cheapflights users on 4/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Wed 5/136:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Deal found 4/22$171
This CheapOair deal was found by Cheapflights users on 4/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:09 pm
MKE
-
BOS
1 stop12h 15m
Multiple Airlines
Tue 5/192:25 pm
BOS
-
MKE
Nonstop2h 38m
Multiple Airlines
Deal found 4/21$174
This Expedia deal was found by Cheapflights users on 4/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Mon 6/16:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Deal found 4/21$180
This Orbitz deal was found by Cheapflights users on 4/19. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Mon 5/186:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Deal found 4/19$181
This Cheapflightsfares deal was found by Cheapflights users on 4/20. 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.
Sat 5/95:17 pm
MKE
-
BOS
Nonstop2h 15m
JetBlue
Mon 5/112:25 pm
BOS
-
MKE
Nonstop2h 38m
JetBlue
Deal found 4/20$182
This Expedia deal was found by Cheapflights users on 4/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/298:41 am
MKE
-
BOS
Nonstop2h 19m
Multiple Airlines
Mon 6/16:00 am
BOS
-
MKE
1 stop6h 14m
Multiple Airlines
Deal found 4/21$184
This Frontier deal was found by Cheapflights users on 4/18. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2212:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Mon 5/256:00 am
BOS
-
MKE
1 stop6h 14m
Frontier
Deal found 4/18$185

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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(Expedia)

One-way from

$76
(Travelocity)

Popular in

February

Cheapest in

September

Average price

$387

Good round-trip deal

$207 or less

Good one-way deal

$118 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
Search Deals
From Milwaukee-Mitchell to Boston Logan Intl
Search Deals
One-way flight from Milwaukee-Mitchell to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Milwaukee-Mitchell to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Milwaukee-Mitchell to Boston Logan Intl.
Search Deals

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 April 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

Price

Cheapest round-trip

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 5/8

1:54 pm-8:26 pm

1 stop5h 32m

Boston Logan Intl

Sun 5/10

5:20 pm-7:08 pm

Nonstop2h 48m

$197

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 5/9

5:00 pm-11:29 pm

1 stop5h 29m

Boston Logan Intl

Tue 5/12

5:20 pm-7:08 pm

Nonstop2h 48m

$197

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 9/8

4:25 pm-10:15 pm

1 stop4h 50m

Boston Logan Intl

Tue 9/15

10:50 am-7:55 pm

2 stops10h 05m

$204
Quickest round-trip

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 6/16

7:10 pm-10:35 pm

Nonstop2h 25m

Boston Logan Intl

Wed 6/17

9:10 am-10:50 am

Nonstop2h 40m

$227

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 6/23

7:10 pm-10:35 pm

Nonstop2h 25m

Boston Logan Intl

Tue 6/30

6:00 pm-11:06 pm

1 stop6h 06m

$237

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 8/14

1:00 pm-7:45 pm

1 stop5h 45m

Boston Logan Intl

Tue 8/18

5:30 am-8:41 am

1 stop4h 11m

$252

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sun 5/31

7:15 pm-1:14 am

1 stop4h 59m

Boston Logan Intl

Thu 6/4

6:00 am-9:57 am

1 stop4h 57m

$267

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 8/14

7:00 pm-1:05 am

1 stop5h 05m

Boston Logan Intl

Tue 8/18

5:59 pm-12:11 am

2 stops7h 12m

$272

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 5/8

5:56 pm-11:35 pm

1 stop4h 39m

Boston Logan Intl

Sun 5/10

5:45 am-1:11 pm

2 stops8h 26m

$272

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 8/4

6:59 pm-10:26 pm

Nonstop2h 27m

Boston Logan Intl

Tue 8/11

5:30 am-8:41 am

1 stop4h 11m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 24 resultsSorted by cheapest first
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust 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?

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 61 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, September is the cheapest month in which you can book a flight from Milwaukee to Boston (average of $256). Flying from Milwaukee to Boston in February is currently the most expensive (average of $419). 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 April 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 48% 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 April 18, 2026.

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

How much does it cost to fly round-trip from Milwaukee to Boston?

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 April 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.
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,327 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,438 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,635 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,952 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,659 reviews
Southwest
8.0
Very good
4,327 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 5 different airlines have flights from Milwaukee-Mitchell (MKE) to Logan Intl (BOS) on a regular basis. There are 3 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 13m.

  • 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?

    Delta and Southwest can get you from Milwaukee to Boston in just under 4h 50m. Your travel time can differ by up to 42m. 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 $88. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $103 and $176, respectively. Users have found that JetBlue is 73% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Milwaukee to Boston one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $78. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Milwaukee to Boston for a low price.

  • 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 EL AL (100%), Delta (90%) or Republic Airways (90%) 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 $91. On average you can expect to pay $232. The most popular route, (Milwaukee-Mitchell - Boston Logan Intl), can usually be booked for $164.

  • 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, September is the cheapest month in which you can book a flight from Milwaukee to Boston (average of $256). Flying from Milwaukee to Boston in February is currently the most expensive (average of $419). 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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
Braintree

Browse thousands of different options on Cheapflights for your next trip

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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 2,558,603 searches. Data last updated April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$88Average$237FlexibilityNo cancel feeOn-time62%
DeltaCheapest$103Average$354FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$258FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$284FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$331FlexibilityNo cancel feeOn-time69%

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