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$92+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Boston Logan Intl are usually found in May 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 September 11, 2025.

Round-trip from

$144
(Southwest)

One-way from

$92
(Southwest)

Popular in

December

Cheapest in

May

Average price

$266

Good round-trip deal

$166 or less

Good one-way deal

$238 or less
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. 13% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 10/306:00 pmMKE - BOS
1 stop4h 55mSouthwest
Tue 11/45:45 amBOS - MKE
1 stop4h 45mSouthwest
Deal found 9/11$144
This Southwest deal was found by Cheapflights users on 9/9. 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 10/183:50 pmMKE - BOS
1 stop4h 45mSouthwest
Wed 10/225:30 amBOS - MKE
1 stop5h 05mSouthwest
Deal found 9/9$154
This Southwest deal was found by Cheapflights users on 9/9. 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 11/105:50 amMKE - BOS
1 stop4h 35mSouthwest
Thu 11/137:20 pmBOS - MKE
1 stop5h 10mSouthwest
Deal found 9/9$160
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:00 amMKE - BOS
1 stop7h 25mSouthwest
Sat 10/45:05 amBOS - MKE
1 stop7h 20mSouthwest
Deal found 9/9$165
This Southwest deal was found by Cheapflights users on 9/9. 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 11/105:50 amMKE - BOS
1 stop4h 35mSouthwest
Wed 11/1212:20 pmBOS - MKE
2 stops10h 05mSouthwest
Deal found 9/9$172
This Southwest deal was found by Cheapflights users on 9/10. 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 11/135:50 amMKE - BOS
1 stop11h 20mSouthwest
Fri 11/146:10 amBOS - MKE
1 stop9h 40mSouthwest
Deal found 9/10$173
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/116:00 amMKE - BOS
1 stop4h 45mSouthwest
Sat 11/157:45 amBOS - MKE
2 stops9h 05mSouthwest
Deal found 9/10$184
This JetBlue deal was found by Cheapflights users on 9/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/174:38 pmMKE - BOS
Nonstop2h 22mJetBlue
Tue 10/212:15 pmBOS - MKE
Nonstop2h 28mJetBlue
Deal found 9/11$187
This Southwest deal was found by Cheapflights users on 9/9. 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 11/135:50 amMKE - BOS
1 stop11h 20mSouthwest
Sat 11/157:45 amBOS - MKE
2 stops9h 05mSouthwest
Deal found 9/9$190
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:05 pmMKE - BOS
1 stop4h 35mSouthwest
Thu 12/47:20 amBOS - MKE
1 stop5h 20mSouthwest
Deal found 9/10$191

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 September 11, 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

Fri 10/24

6:00 pm-11:55 pm

1 stop4h 55m

Boston Logan Intl

Tue 10/28

5:30 am-9:35 am

1 stop5h 05m

$167

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 11/13

5:50 am-6:10 pm

1 stop11h 20m

Boston Logan Intl

Fri 11/14

6:10 am-2:50 pm

1 stop9h 40m

$173

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 12/2

11:30 am-9:05 pm

2 stops8h 35m

Boston Logan Intl

Thu 12/4

5:15 pm-9:30 pm

1 stop5h 15m

$204

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 9/26

3:44 pm-9:45 pm

1 stop5h 01m

Boston Logan Intl

Sat 9/27

12:35 pm-5:06 pm

1 stop5h 31m

$207

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 10/23

2:05 pm-11:00 pm

1 stop7h 55m

Boston Logan Intl

Tue 10/28

9:15 am-1:13 pm

1 stop4h 58m

$237

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 10/22

11:15 am-9:10 pm

2 stops8h 55m

Boston Logan Intl

Sat 10/25

6:30 am-3:40 pm

1 stop10h 10m

$251

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Fri 10/24

4:49 pm-11:49 pm

1 stop6h 00m

Boston Logan Intl

Tue 10/28

9:35 am-11:18 am

Nonstop2h 43m

$263

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Mon 11/3

6:40 am-4:35 pm

1 stop8h 55m

Boston Logan Intl

Mon 11/3

5:35 pm-9:45 pm

1 stop5h 10m

$266

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Mon 9/29

7:50 pm-11:15 pm

Nonstop2h 25m

Boston Logan Intl

Wed 10/1

6:00 am-12:23 pm

1 stop7h 23m

$267

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sun 10/26

6:45 pm-12:15 am

1 stop4h 30m

Boston Logan Intl

Wed 10/29

5:15 am-11:30 am

2 stops7h 15m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 21 results
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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 August 29, 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, January is the cheapest month in which you can book a flight from Milwaukee to Boston (average of $218). Flying from Milwaukee to Boston in July is currently the most expensive (average of $311). 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 September 11, 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 47% on your trip compared to booking a flight in the morning.

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 September 7, 2025.

Travelers seeking maximum savings on their Milwaukee to Boston flight should consider departing on Saturday evenings 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 September 11, 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
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Entertainment

7.5

Comfort

8.0

Food

7.0

Boarding

8.1

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 7 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 17m.

  • How popular is this Milwaukee to Boston flight route?

    This flight path from Milwaukee-Mitchell to Boston Logan Intl was viewed by 6 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 United Airlines can get you from Milwaukee to Boston in just under 4h 55m. Your travel time can differ by up to 06m. 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 $119. Additional round-trip tickets that might be worth considering are offered by Spirit Airlines and Delta, with the lowest prices starting at $164 and $164, respectively. Users have found that JetBlue is 62% 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 Southwest, with whom users have recently found tickets for as low as $92. However, be on the lookout for offers from JetBlue 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 Air France (88%), Delta (79%) or Republic Airways (79%) 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 $281. The most popular route, (Milwaukee-Mitchell - Boston Logan Intl), can usually be booked for $160.

  • 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, January is the cheapest month in which you can book a flight from Milwaukee to Boston (average of $218). Flying from Milwaukee to Boston in July is currently the most expensive (average of $311). 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
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Waltham
Saugus
Burlington

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$119Average$280FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$164Average$267FlexibilityNo cancel feeOn-time65%
DeltaCheapest$164Average$381FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$186Average$299FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$186Average$284FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$186Average$271FlexibilityNo cancel feeOn-time71%

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