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Wisconsin

$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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(JetBlue)

One-way from

$59
(Delta)

Popular in

November

Cheapest in

September

Average price

$466

Good round-trip deal

$319 or less

Good one-way deal

$208 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. 13% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This Delta deal was found by Cheapflights users on 11/6. 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 12/127:52 pmBOS - ORD
Nonstop2h 55mDelta
Sun 12/147:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 11/6$117
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Wed 11/127:19 pmBOS - ORD
Nonstop3h 06mAmerican Airlines
Wed 12/38:40 pmORD - BOS
Nonstop2h 33mAmerican Airlines
Deal found 11/5$118
This Kissandfly.com deal was found by Cheapflights users on 11/6. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:30 amBOS - ORD
Nonstop3h 05mJetBlue
Wed 12/177:00 amORD - BOS
1 stop7h 14mJetBlue
Deal found 11/6$119
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 12/1111:28 amBOS - ORD
1 stop6h 59mFrontier
Thu 12/256:00 amORD - BOS
1 stop18h 19mFrontier
Deal found 11/5$120
This JetBlue deal was found by Cheapflights users on 11/6. 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 12/45:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 11/6$122
This Delta deal was found by Cheapflights users on 11/6. 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 12/127:52 pmBOS - ORD
Nonstop2h 55mDelta
Fri 12/197:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 11/6$124
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:30 amBOS - ORD
Nonstop3h 05mJetBlue
Tue 12/1611:25 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 11/6$125
This JetBlue deal was found by Cheapflights users on 11/6. 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.
Sat 12/63:40 pmBOS - ORD
1 stop7h 12mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 11/6$126
This United Airlines deal was found by Cheapflights users on 11/5. 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.
Thu 11/139:40 amBOS - ORD
Nonstop3h 00mUnited Airlines
Sun 11/166:15 amORD - BOS
Nonstop2h 15mUnited Airlines
Deal found 11/5$127
This Priceline deal was found by Cheapflights users on 11/5. 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 12/1111:28 amBOS - ORD
1 stop6h 59mFrontier
Sun 12/146:00 amORD - BOS
1 stop5h 02mFrontier
Deal found 11/5$128
This FlightHub deal was found by Cheapflights users on 11/5. 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 12/1811:49 amBOS - MSP
Nonstop3h 11mSun Country Air
Mon 12/225:24 amMSP - BOS
Nonstop2h 59mSun Country Air
Deal found 11/5$188
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Wed 12/1010:56 amBOS - MKE
1 stop23h 43mMultiple Airlines
Fri 12/126:09 pmMKE - BOS
1 stop14h 52mMultiple Airlines
Deal found 11/5$189

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 November 6, 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 12/11

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Fri 12/26

7:41 pm-11:10 pm

Nonstop2h 29m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 12/6

3:40 pm-9:52 pm

1 stop7h 12m

Chicago O'Hare Intl

Mon 12/8

8:38 pm-12:06 am

Nonstop2h 28m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 11/21

5:00 am-12:15 pm

1 stop8h 15m

Chicago O'Hare Intl

Tue 12/2

1:45 pm-10:15 pm

1 stop7h 30m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/9

9:40 am-11:40 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 12/22

9:12 pm-12:45 am

Nonstop2h 33m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/16

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Sun 12/21

7:41 pm-11:10 pm

Nonstop2h 29m

$143

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/16

5:00 am-12:15 pm

1 stop8h 15m

Chicago O'Hare Intl

Mon 1/26

1:45 pm-9:45 pm

1 stop7h 00m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

7:07 pm-11:44 pm

1 stop5h 37m

Chicago O'Hare Intl

Sat 12/6

11:00 am-2:20 pm

Nonstop2h 20m

$148

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/2

7:45 am-9:49 am

Nonstop3h 04m

Chicago O'Hare Intl

Sun 1/4

9:12 pm-12:45 am

Nonstop2h 33m

$151

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/18

7:45 am-9:49 am

Nonstop3h 04m

Chicago O'Hare Intl

Tue 12/23

9:12 pm-12:45 am

Nonstop2h 33m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

3:40 pm-9:52 pm

1 stop7h 12m

Chicago O'Hare Intl

Fri 12/12

8:38 pm-12:06 am

Nonstop2h 28m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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, September is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $98). Flying from Massachusetts to Wisconsin in February is currently the most expensive (average of $272). 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 November 6, 2025.

When flying from Massachusetts to Wisconsin, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 23% versus a flight in the afternoon.

What is the cheapest day to fly from Massachusetts to Wisconsin?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Wisconsin. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Wisconsin flight should consider departing on Monday mornings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 6, 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
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
9,007 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
11,040 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
2,907 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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 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 3h. JetBlue provides one of the quickest options available for as low as $136. 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 Delta ($59), United Airlines ($64), and Sun Country Air ($99).

  • 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, September is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $98). Flying from Massachusetts to Wisconsin in February is currently the most expensive (average of $272). 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$294FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$145Average$187FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$292FlexibilityNo cancel feeOn-time63%
DeltaCheapest$186Average$482FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$444FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$202Average$446FlexibilityNo cancel feeOn-time69%

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