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$59+ Cheap flights from Massachusetts to Wisconsin

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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
abr. 27 — may. 41
dom. 4/27
dom. 5/4
1 adult, Economy
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Cheap flight deals from Massachusetts to Wisconsin

Keep the following information in mind while searching for Massachusetts to Wisconsin flight deals. Data was last updated abril 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$129
(Cheapflightsfares)

One-way from

$59
(JetBlue)

Popular in

December

Cheapest in

August

Average price

$339

Good round-trip deal

$219 or less

Good one-way deal

$138 or less
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Milwaukee-Mitchell flights.
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From Massachusetts to Wisconsin
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One-way flight from Massachusetts to Wisconsin
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Highest demand for flights based on searches. 14% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Massachusetts to Wisconsin.
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Price to beat on a one-way flight from Massachusetts to Wisconsin.
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Find flight deals from Massachusetts to Wisconsin

Cheapest flights from Massachusetts to Wisconsin
Explore the most affordable flight options available from Massachusetts to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 22, 2025.

This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/95:42 pmBOS - ORD
1 stop6h 47mSpirit Airlines
mié. 5/1412:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Deal found 4/21$129
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/76:45 amBOS - ORD
1 stop9h 15mSouthwest
mié. 6/114:00 pmORD - BOS
1 stop6h 55mSouthwest
Deal found 4/21$136
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/57:45 amBOS - ORD
Nonstop2h 58mUnited Airlines
lun. 6/96:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 4/21$137
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/16:10 amBOS - ORD
Nonstop3h 08mAmerican Airlines
lun. 5/54:40 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Deal found 4/22$147
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/56:00 amBOS - ORD
Nonstop3h 00mJetBlue
mar. 6/107:31 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 4/21$152
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/143:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
sáb. 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Deal found 4/21$153
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/78:20 pmBOS - ORD
Nonstop2h 54mDelta
dom. 5/117:00 amORD - BOS
Nonstop2h 25mDelta
Deal found 4/20$180
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/212:08 pmBOS - MKE
Nonstop2h 40mJetBlue
mié. 5/284:43 pmMKE - BOS
Nonstop2h 16mJetBlue
Deal found 4/21$187
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/95:10 pmBOS - MKE
Nonstop2h 46mDelta
mar. 5/137:40 pmMKE - BOS
Nonstop2h 19mDelta
Deal found 4/22$197
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/298:47 amBOS - ORD
1 stop9h 21mFrontier
dom. 6/15:14 pmORD - BOS
1 stop14h 21mFrontier
Deal found 4/21$200
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/64:45 pmBOS - MKE
1 stop6h 30mUnited Airlines
mié. 5/710:15 amMKE - BOS
1 stop5h 02mUnited Airlines
Deal found 4/22$202
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/2210:15 amBOS - MSP
1 stop10h 42mMultiple Airlines
mar. 5/276:54 amMSP - BOS
Nonstop2h 48mMultiple Airlines
Deal found 4/21$220

Cheapflights Fare Finder

Customize your flight search to find flights from Massachusetts to Wisconsin 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 abril 22, 2025.
Use the filters below to find and compare flights from Massachusetts to Wisconsin that are best for you.

Fly from

Massachusetts

Fly to

Wisconsin

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 5/20

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

mié. 5/21

12:41 pm-11:29 pm

1 stop9h 48m

$118

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 6/7

6:45 am-3:00 pm

1 stop9h 15m

Chicago O'Hare Intl

mié. 6/11

4:00 pm-11:55 pm

1 stop6h 55m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 5/6

7:45 am-9:42 am

Nonstop2h 57m

Chicago O'Hare Intl

jue. 5/8

1:55 pm-5:19 pm

Nonstop2h 24m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 4/30

5:00 am-7:00 am

Nonstop3h 00m

Chicago O'Hare Intl

vie. 5/2

4:49 pm-8:09 pm

Nonstop2h 20m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 6/5

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

sáb. 6/14

9:40 am-1:09 pm

Nonstop2h 29m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 5/14

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

sáb. 5/17

4:15 pm-12:44 am

1 stop7h 29m

$153

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 7/2

8:05 pm-10:05 pm

Nonstop3h 00m

Chicago O'Hare Intl

mar. 7/8

10:10 am-1:40 pm

Nonstop2h 30m

$177

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

mié. 5/21

2:08 pm-3:48 pm

Nonstop2h 40m

Milwaukee-Mitchell

mié. 5/28

4:43 pm-7:59 pm

Nonstop2h 16m

$187

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 5/10

8:00 am-11:32 pm

1 stop16h 32m

Chicago O'Hare Intl

lun. 5/12

4:15 pm-12:44 am

1 stop7h 29m

$189

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

vie. 5/9

5:10 pm-6:56 pm

Nonstop2h 46m

Milwaukee-Mitchell

mar. 5/13

7:40 pm-10:59 pm

Nonstop2h 19m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Massachusetts 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 Massachusetts to Wisconsin

What is the cheapest month to book a flight from Massachusetts to Wisconsin?

Currently, February is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $280). Flying from Massachusetts to Wisconsin in June is currently the most expensive (average of $376). 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 MA to WI?

Find hourly flight availability from Massachusetts to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 22, 2025.

When flying from Massachusetts to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated abril 22, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Massachusetts to Wisconsin have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,906 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,906 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,683 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Overall

8.0

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Massachusetts to Wisconsin one-way?

    The cheapest airlines for a one-way flight from Massachusetts to Wisconsin are JetBlue ($59), United Airlines ($64), and Southwest ($68).

  • Can I find deals for flights from Massachusetts to Wisconsin that include hotel bookings?

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

  • How can I find direct flights from Massachusetts to Wisconsin?

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

  • Can I find deals for business class flights from Massachusetts to Wisconsin?

    Yes. Cheapflights offers flight deals from Massachusetts to Wisconsin 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 Massachusetts to Wisconsin?

    Currently, February is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $280). Flying from Massachusetts to Wisconsin in June is currently the most expensive (average of $376). 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

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Alternative routes for Massachusetts to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Massachusetts to Wisconsin

Discover the top 6 airlines that operate flights from Massachusetts to Wisconsin. 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 abril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$172FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$154Average$316FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$176Average$460FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$458FlexibilityNo cancel feeOn-time69%
DeltaCheapest$204Average$546FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$226Average$377FlexibilityNo cancel feeOn-time63%

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