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Wisconsin

$63+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Jun 20 — Jun 271
Fri 6/20
Fri 6/27
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 June 15, 2025.

Round-trip from

$124
(eDestinos)

One-way from

$63
(JetBlue)

Popular in

December

Cheapest in

August

Average price

$306

Good round-trip deal

$234 or less

Good one-way deal

$134 or less
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. 15% potential increase in price ($64 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 June 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 June 15, 2025.

This eDestinos deal was found by Cheapflights users on 6/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/306:15 amBOS - ORD
1 stop13h 29mSpirit Airlines
Wed 7/910:00 amORD - BOS
1 stop8h 30mSpirit Airlines
Deal found 6/14$124
This JetBlue deal was found by Cheapflights users on 6/13. 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.
Mon 8/186:00 amBOS - ORD
Nonstop2h 55mJetBlue
Mon 8/258:40 amORD - BOS
Nonstop2h 25mJetBlue
Deal found 6/13$125
This American Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 9/115:00 amBOS - ORD
Nonstop2h 51mAmerican Airlines
Sun 9/146:05 amORD - BOS
Nonstop2h 27mAmerican Airlines
Deal found 6/13$141
This Southwest deal was found by Cheapflights users on 6/13. 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 7/15:45 amBOS - ORD
1 stop6h 15mSouthwest
Sat 7/127:30 amORD - BOS
1 stop7h 20mSouthwest
Deal found 6/13$142
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Tue 7/17:04 pmBOS - ORD
1 stop5h 33mUnited Airlines
Fri 7/42:28 pmORD - BOS
Nonstop2h 38mUnited Airlines
Deal found 6/13$143
This Sun Country Air deal was found by Cheapflights users on 6/13. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/611:46 amBDL - MSP
Nonstop3h 02mSun Country Air
Sun 7/137:18 amMSP - BDL
Nonstop2h 35mSun Country Air
Deal found 6/13$148
This Delta deal was found by Cheapflights users on 6/15. 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.
Thu 7/247:20 amBOS - ORD
Nonstop2h 58mDelta
Fri 8/87:10 pmORD - BOS
Nonstop2h 40mDelta
Deal found 6/15$155
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Tue 7/298:08 amBOS - MKE
1 stop4h 36mAmerican Airlines
Tue 8/55:57 pmMKE - BOS
1 stop5h 17mAmerican Airlines
Deal found 6/14$176
This JetBlue deal was found by Cheapflights users on 6/13. 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.
Tue 8/261:01 pmBOS - MKE
Nonstop2h 30mJetBlue
Wed 8/273:30 pmMKE - BOS
Nonstop2h 15mJetBlue
Deal found 6/13$177
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 7/58:02 pmBOS - MKE
1 stop4h 52mUnited Airlines
Tue 7/158:35 amMKE - BOS
2 stops6h 54mUnited Airlines
Deal found 6/15$182
This Booking.com deal was found by Cheapflights users on 6/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1111:40 amBDL - MSP
Nonstop3h 02mMultiple Airlines
Fri 7/181:21 pmMSP - BDL
1 stop8h 36mMultiple Airlines
Deal found 6/15$187
This Southwest deal was found by Cheapflights users on 6/13. 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 6/306:10 amBOS - MKE
1 stop5h 35mSouthwest
Tue 7/85:25 pmMKE - BOS
1 stop5h 30mSouthwest
Deal found 6/13$187

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 June 15, 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

Mon 6/30

6:15 am-6:44 pm

1 stop13h 29m

Chicago O'Hare Intl

Wed 7/9

10:00 am-7:30 pm

1 stop8h 30m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 8/18

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Mon 8/25

8:40 am-12:05 pm

Nonstop2h 25m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/4

3:15 pm-5:10 pm

Nonstop2h 55m

Chicago O'Hare Intl

Tue 7/8

10:20 am-1:54 pm

Nonstop2h 34m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/11

5:00 am-6:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Sun 9/14

6:05 am-9:32 am

Nonstop2h 27m

$141

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/1

5:45 am-11:00 am

1 stop6h 15m

Chicago O'Hare Intl

Sat 7/12

7:30 am-3:50 pm

1 stop7h 20m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/1

7:04 pm-11:37 pm

1 stop5h 33m

Chicago O'Hare Intl

Fri 7/4

2:28 pm-6:06 pm

Nonstop2h 38m

$143

HartfordMinneapolis

BDL - MSP

BDLMSP

Hartford Bradley Intl

Sun 7/6

11:46 am-1:48 pm

Nonstop3h 02m

Minneapolis St Paul

Sun 7/13

7:18 am-10:53 am

Nonstop2h 35m

$148

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 7/29

8:08 am-11:44 am

1 stop4h 36m

Milwaukee-Mitchell

Tue 8/5

5:57 pm-12:14 am

1 stop5h 17m

$176

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Tue 8/26

1:01 pm-2:31 pm

Nonstop2h 30m

Milwaukee-Mitchell

Wed 8/27

3:30 pm-6:45 pm

Nonstop2h 15m

$177

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Sat 7/5

8:02 pm-11:54 pm

1 stop4h 52m

Milwaukee-Mitchell

Tue 7/15

8:35 am-4:29 pm

2 stops6h 54m

$182

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

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 June 15, 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.

Weekly flight availability from Massachusetts to Wisconsin

Explore weekly flight availability from Massachusetts to Wisconsin. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 15, 2025.

The most flights from USMA to USWI are scheduled on a Wednesday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 June 15, 2025.
See what other customers who have flown with Breeze Airways, Alaska Airlines and Southwest 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.
Breeze Airways
8.1
Very good
179 reviews

Boarding

8.3

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
179 reviews
Breeze Airways
8.1
Very good
179 reviews

Boarding

8.3

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Alaska Airlines
8.0
Very good
10,000 reviews
Breeze Airways
8.1
Very good
179 reviews

Boarding

8.3

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,285 reviews
Breeze Airways
8.1
Very good
179 reviews

Boarding

8.3

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,963 reviews
Breeze Airways
8.1
Very good
179 reviews

Boarding

8.3

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,798 reviews
Breeze Airways
8.1
Very good
179 reviews

Boarding

8.3

Entertainment

6.6

Food

6.7

Crew

8.8

Comfort

8.2

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 ($63), Spirit Airlines ($68), and Sun Country Air ($69).

  • 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 June 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$175FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$144Average$300FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$186Average$491FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$186Average$447FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$534FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$196Average$356FlexibilityNo cancel feeOn-time63%

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