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Wisconsin

$68+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 30, 2025.

Round-trip from

$132
(Priceline)

One-way from

$68
(FlightHub)

Popular in

December

Cheapest in

August

Average price

$306

Good round-trip deal

$224 or less

Good one-way deal

$113 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. 16% potential increase in price ($65 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 30, 2025.

This Priceline deal was found by Cheapflights users on 6/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/229:20 amBOS - ORD
1 stop10h 21mMultiple Airlines
Tue 8/2611:36 amORD - BOS
1 stop11h 13mMultiple Airlines
Deal found 6/27$132
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/298:39 pmBOS - ORD
1 stop13h 16mSpirit Airlines
Tue 8/1210:00 amORD - BOS
1 stop8h 30mSpirit Airlines
Deal found 6/30$135
This Aviatur deal was found by Cheapflights users on 6/29. 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 Aviatur is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/257:00 amBOS - ORD
Nonstop2h 57mJetBlue
Tue 9/309:42 amORD - BOS
Nonstop2h 28mJetBlue
Deal found 6/29$136
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/145:28 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Thu 8/217:00 amORD - BOS
Nonstop2h 24mAmerican Airlines
Deal found 6/30$138
This Southwest deal was found by Cheapflights users on 6/30. 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.
Mon 9/17:30 amBOS - ORD
1 stop6h 15mSouthwest
Tue 9/21:50 pmORD - BOS
1 stop7h 35mSouthwest
Deal found 6/30$142
This United Airlines deal was found by Cheapflights users on 6/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/157:04 pmBOS - ORD
1 stop5h 37mUnited Airlines
Wed 7/168:05 pmORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 6/29$143
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/249:20 amBOS - ORD
1 stop10h 21mFrontier
Thu 8/287:46 pmORD - BOS
1 stop11h 49mFrontier
Deal found 6/30$145
This Sun Country Air deal was found by Cheapflights users on 6/29. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3111:52 amBDL - MSP
Nonstop3h 02mSun Country Air
Sun 8/37:12 amMSP - BDL
Nonstop2h 35mSun Country Air
Deal found 6/29$148
This Delta deal was found by Cheapflights users on 6/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/234:05 pmBOS - ORD
Nonstop3h 06mDelta
Mon 8/117:00 amORD - BOS
Nonstop2h 29mDelta
Deal found 6/28$155
This JetBlue deal was found by Cheapflights users on 6/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/271:40 pmBOS - MKE
Nonstop2h 28mJetBlue
Sat 8/305:38 pmMKE - BOS
Nonstop2h 12mJetBlue
Deal found 6/28$157
This FlightHub deal was found by Cheapflights users on 6/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/316:20 amBDL - MSP
1 stop6h 56mMultiple Airlines
Sun 8/37:12 amMSP - BDL
Nonstop2h 35mMultiple Airlines
Deal found 6/28$171
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:00 amBOS - MKE
1 stop7h 20mSouthwest
Mon 8/255:15 amMKE - BOS
1 stop7h 35mSouthwest
Deal found 6/29$177

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 30, 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

Fri 8/22

9:20 am-6:41 pm

1 stop10h 21m

Chicago O'Hare Intl

Tue 8/26

11:36 am-11:49 pm

1 stop11h 13m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/29

8:39 pm-8:55 am

1 stop13h 16m

Chicago O'Hare Intl

Tue 8/12

10:00 am-7:30 pm

1 stop8h 30m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/25

7:00 am-8:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Tue 9/30

9:42 am-1:10 pm

Nonstop2h 28m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/14

5:28 am-7:24 am

Nonstop2h 56m

Chicago O'Hare Intl

Thu 8/21

7:00 am-10:24 am

Nonstop2h 24m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/1

7:30 am-12:45 pm

1 stop6h 15m

Chicago O'Hare Intl

Tue 9/2

1:50 pm-10:25 pm

1 stop7h 35m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 8/24

9:20 am-6:41 pm

1 stop10h 21m

Chicago O'Hare Intl

Thu 8/28

7:46 pm-8:35 am

1 stop11h 49m

$145

HartfordMinneapolis

BDL - MSP

BDLMSP

Hartford Bradley Intl

Thu 7/31

11:52 am-1:54 pm

Nonstop3h 02m

Minneapolis St Paul

Sun 8/3

7:12 am-10:47 am

Nonstop2h 35m

$148

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/23

4:05 pm-6:11 pm

Nonstop3h 06m

Chicago O'Hare Intl

Mon 8/11

7:00 am-10:29 am

Nonstop2h 29m

$155

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Wed 8/27

1:40 pm-3:08 pm

Nonstop2h 28m

Milwaukee-Mitchell

Sat 8/30

5:38 pm-8:50 pm

Nonstop2h 12m

$157

HartfordMinneapolis

BDL - MSP

BDLMSP

Hartford Bradley Intl

Thu 7/31

6:20 am-12:16 pm

1 stop6h 56m

Minneapolis St Paul

Sun 8/3

7:12 am-10:47 am

Nonstop2h 35m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

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 30, 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 30, 2025.

The most flights from USMA to USWI are scheduled on a Sunday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 30, 2025.
Get a feel of what it's like to fly with Breeze Airways, Southwest, and Delta from Massachusetts to Wisconsin by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
182 reviews

Food

6.8

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.4

Comfort

8.2

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
182 reviews
Breeze Airways
8.1
Very good
182 reviews

Food

6.8

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.4

Comfort

8.2

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
4,278 reviews
Breeze Airways
8.1
Very good
182 reviews

Food

6.8

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.4

Comfort

8.2

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
7,973 reviews
Breeze Airways
8.1
Very good
182 reviews

Food

6.8

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.4

Comfort

8.2

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
8,852 reviews
Breeze Airways
8.1
Very good
182 reviews

Food

6.8

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.4

Comfort

8.2

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!
JetBlue
7.3
Good
2,920 reviews
Breeze Airways
8.1
Very good
182 reviews

Food

6.8

Crew

8.8

Entertainment

6.6

Overall

8.1

Boarding

8.4

Comfort

8.2

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 Spirit Airlines ($68), Sun Country Air ($69), and JetBlue ($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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$175FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$135Average$297FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$186Average$329FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$491FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$186Average$449FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$526FlexibilityNo cancel feeOn-timeN/A

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