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$57+ 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 6/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Apr 30 — May 71
Thu 4/30
Thu 5/7
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 May, booked 63 days in advance, depart on a Friday or Saturday 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 March 31, 2026.

This Southwest deal was found by Cheapflights users on 3/30. 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 4/299:15 am
MKE
-
BOS
1 stop7h 00m
Southwest
Wed 5/65:55 pm
BOS
-
MKE
1 stop5h 20m
Southwest
Deal found 3/30$157
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Sat 5/25:41 pm
MKE
-
BOS
1 stop5h 44m
American Airlines
Tue 5/55:09 pm
BOS
-
MKE
1 stop5h 32m
American Airlines
Deal found 3/31$159
This Frontier deal was found by Cheapflights users on 3/27. 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 3/27$160
This Southwest deal was found by Cheapflights users on 3/26. 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.
Wed 4/295:50 am
MKE
-
BOS
2 stops7h 00m
Southwest
Sat 5/25:25 am
BOS
-
MKE
2 stops7h 25m
Southwest
Deal found 3/26$161
This Delta deal was found by Cheapflights users on 3/31. 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 4/296:00 am
MKE
-
BOS
1 stop6h 24m
Delta
Sun 5/31:30 pm
BOS
-
MKE
1 stop7h 55m
Delta
Deal found 3/31$162
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/14:26 pm
MKE
-
BOS
1 stop6h 59m
American Airlines
Mon 5/45:40 pm
BOS
-
MKE
1 stop6h 17m
American Airlines
Deal found 3/31$163
This Priceline deal was found by Cheapflights users on 3/29. 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.
Fri 4/175:13 pm
MKE
-
BOS
1 stop7h 18m
Multiple Airlines
Fri 5/12:25 pm
BOS
-
MKE
Nonstop2h 36m
Multiple Airlines
Deal found 3/29$164
This Delta deal was found by Cheapflights users on 3/30. 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 5/86:43 pm
MKE
-
BOS
1 stop3h 46m
Delta
Sun 5/105:40 am
BOS
-
MKE
1 stop4h 09m
Delta
Deal found 3/30$167
This CheapOair deal was found by Cheapflights users on 3/30. 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 5/278:41 am
MKE
-
BOS
Nonstop2h 19m
Multiple Airlines
Sat 5/306:00 am
BOS
-
MKE
1 stop6h 34m
Multiple Airlines
Deal found 3/30$169
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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.
Thu 4/304:35 pm
MKE
-
BOS
Nonstop2h 15m
JetBlue
Mon 5/42:25 pm
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 3/30$172
This KAYAK deal was found by Cheapflights users on 3/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:41 am
MKE
-
BOS
Nonstop2h 19m
JetBlue
Mon 6/86:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 3/28$177

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 March 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Southwest)

One-way from

$58
(Cheapflightsfares)

Popular in

February

Cheapest in

September

Average price

$368

Good round-trip deal

$212 or less

Good one-way deal

$208 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 ($63 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 March 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 March 31, 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

Thu 4/30

7:10 am-3:28 pm

1 stop7h 18m

Boston Logan Intl

Mon 5/4

3:00 pm-9:30 pm

1 stop7h 30m

$207

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sun 4/12

5:10 am-11:01 am

1 stop4h 51m

Boston Logan Intl

Mon 4/27

6:48 pm-11:43 pm

1 stop5h 55m

$225
Quickest round-trip

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 6/23

4:52 pm-11:54 pm

1 stop6h 02m

Boston Logan Intl

Tue 6/30

5:30 am-8:51 am

1 stop4h 21m

$252

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 5/27

1:30 pm-11:59 pm

2 stops9h 29m

Boston Logan Intl

Sat 5/30

6:00 am-10:09 am

1 stop5h 09m

$252

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 9/17

2:00 pm-10:27 pm

1 stop7h 27m

Boston Logan Intl

Mon 9/21

6:00 am-10:07 am

1 stop5h 07m

$257

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 8/4

5:00 am-2:40 pm

2 stops8h 40m

Boston Logan Intl

Tue 8/11

6:00 am-10:00 am

1 stop5h 00m

$287

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 5/22

7:00 pm-12:59 am

1 stop4h 59m

Boston Logan Intl

Sat 6/6

6:00 am-4:42 pm

3 stops11h 42m

$292

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 5/20

9:15 am-5:15 pm

1 stop7h 00m

Boston Logan Intl

Sat 5/23

5:25 am-11:50 am

2 stops7h 25m

$302

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 5/21

5:29 pm-12:59 am

1 stop6h 30m

Boston Logan Intl

Sun 5/24

5:45 am-12:48 pm

2 stops8h 03m

$307
Cheapest one-way

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 4/30

4:50 pm-10:20 pm

1 stop4h 30m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 March.
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?

Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to Boston. Price data was last updated on March 13, 2026.

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, September is the cheapest month in which you can book a flight from Milwaukee to Boston (average of $91). Flying from Milwaukee to Boston in January is currently the most expensive (average of $117). 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 March 31, 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 44% 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 March 28, 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 March 31, 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
4,332 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
4,332 reviews
Southwest
8.0
Very good
4,332 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
8,364 reviews
Southwest
8.0
Very good
4,332 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
9,525 reviews
Southwest
8.0
Very good
4,332 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
2,906 reviews
Southwest
8.0
Very good
4,332 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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
11,543 reviews
Southwest
8.0
Very good
4,332 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

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 5 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?

    JetBlue and Delta can get you from Milwaukee to Boston in just under 2h 19m. Your travel time can differ by up to 4h 59m. 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 $90. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $106 and $176, respectively. Users have found that JetBlue is 72% 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%), KLM (90%) or Delta (89%) 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 $88. On average you can expect to pay $409. The most popular route, (Milwaukee-Mitchell - Boston Logan Intl), can usually be booked for $116.

  • 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 $91). Flying from Milwaukee to Boston in January is currently the most expensive (average of $117). 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
Seabrook
Cranston
Chelsea
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Lincoln
Quincy
Lowell

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 March 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$90Average$258FlexibilityNo cancel feeOn-time62%
DeltaCheapest$106Average$355FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$264FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$282FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$206Average$326FlexibilityNo cancel feeOn-time69%

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