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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 9/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$135
(Priceline)

One-way from

$68
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$292

Good round-trip deal

$212 or less

Good one-way deal

$158 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. 17% potential increase in price ($74 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 August 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 August 18, 2025.

This Priceline deal was found by Cheapflights users on 8/18. 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.
Thu 9/48:47 amBOS - ORD
1 stop9h 04mMultiple Airlines
Tue 9/911:57 amORD - BOS
1 stop11h 00mMultiple Airlines
Deal found 8/18$135
This FlightHub deal was found by Cheapflights users on 8/16. 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 9/46:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Tue 9/911:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/16$136
This Delta deal was found by Cheapflights users on 8/18. 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 9/127:30 pmBOS - ORD
Nonstop2h 45mDelta
Sat 9/207:25 amORD - BOS
Nonstop2h 30mDelta
Deal found 8/18$137
This American Airlines deal was found by Cheapflights users on 8/17. 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 9/185:00 amBOS - ORD
Nonstop2h 51mAmerican Airlines
Mon 9/226:05 amORD - BOS
Nonstop2h 27mAmerican Airlines
Deal found 8/17$138
This Mytrip deal was found by Cheapflights users on 8/17. 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.
Wed 10/16:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Wed 10/86:00 amORD - BOS
1 stop6h 44mSpirit Airlines
Deal found 8/17$140
This FlightHub deal was found by Cheapflights users on 8/17. 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.
Tue 9/93:00 pmBOS - ORD
1 stop8h 48mMultiple Airlines
Fri 9/126:21 pmORD - BOS
1 stop12h 22mMultiple Airlines
Deal found 8/17$143
This Orbitz deal was found by Cheapflights users on 8/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1012:20 pmBOS - ORD
1 stop10h 38mMultiple Airlines
Fri 9/126:21 pmORD - BOS
1 stop12h 22mMultiple Airlines
Deal found 8/16$145
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
Wed 9/1711:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/15$146
This Priceline deal was found by Cheapflights users on 8/17. 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.
Sat 9/132:15 pmBOS - MKE
Nonstop2h 28mJetBlue
Sat 9/204:38 pmMKE - BOS
Nonstop2h 39mJetBlue
Deal found 8/17$147
This JetBlue deal was found by Cheapflights users on 8/18. 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.
Thu 9/47:00 amBOS - ORD
Nonstop2h 56mJetBlue
Thu 9/119:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 8/18$147
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 9/233:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Wed 10/111:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/17$148
This JetBlue deal was found by Cheapflights users on 8/18. 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 9/21:40 pmBOS - MKE
Nonstop2h 28mJetBlue
Sat 9/64:38 pmMKE - BOS
Nonstop2h 39mJetBlue
Deal found 8/18$157

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 August 18, 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

Thu 9/4

8:47 am-4:51 pm

1 stop9h 04m

Chicago O'Hare Intl

Tue 9/9

11:57 am-11:57 pm

1 stop11h 00m

$135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/2

6:05 am-7:07 pm

1 stop14h 02m

Chicago O'Hare Intl

Tue 9/9

11:57 am-11:57 pm

1 stop11h 00m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/25

8:47 pm-10:35 pm

Nonstop2h 48m

Chicago O'Hare Intl

Mon 9/29

6:30 am-9:56 am

Nonstop2h 26m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/22

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 9/30

9:51 am-1:20 pm

Nonstop2h 29m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/13

7:25 am-9:15 am

Nonstop2h 50m

Chicago O'Hare Intl

Wed 9/17

10:15 am-1:49 pm

Nonstop2h 34m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/26

5:00 am-6:51 am

Nonstop2h 51m

Chicago O'Hare Intl

Mon 9/29

8:25 pm-11:53 pm

Nonstop2h 28m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/22

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sat 9/27

9:51 am-1:20 pm

Nonstop2h 29m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 9/13

7:25 am-9:15 am

Nonstop2h 50m

Chicago O'Hare Intl

Tue 9/16

2:05 pm-5:44 pm

Nonstop2h 39m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 10/25

7:20 am-9:22 am

Nonstop3h 02m

Chicago O'Hare Intl

Tue 10/28

3:50 pm-7:23 pm

Nonstop2h 33m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/1

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 10/8

6:50 pm-10:23 pm

Nonstop2h 33m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

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 August 18, 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 August 18, 2025.

The most flights from USMA to USWI are scheduled on a Sunday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 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 August 18, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines 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.
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
JetBlue
7.2
Good
2,915 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • How long is the flight from Massachusetts to Wisconsin?

    A quick flight from Massachusetts to Wisconsin can take about 2h 48m. Spirit Airlines provides one of the quickest options available for as low as $137. Airlines will cover a distance of 864 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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), Frontier ($73), and American Airlines ($79).

  • 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$112Average$187FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$123Average$297FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$307FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$484FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$455FlexibilityNo cancel feeOn-time71%
DeltaCheapest$200Average$502FlexibilityNo cancel feeOn-timeN/A

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