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Wisconsin

$62+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Dec 29 — Jan 51
Mon 12/29
Mon 1/5
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 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$62
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$493

Good round-trip deal

$378 or less

Good one-way deal

$228 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. 15% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($14 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 29, 2025.

This JetBlue deal was found by Cheapflights users on 11/28. 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.
Sat 12/68:30 amBOS - ORD
Nonstop3h 05mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 11/28$127
This JetBlue deal was found by Cheapflights users on 11/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:30 amBOS - ORD
Nonstop3h 05mJetBlue
Thu 12/187:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 11/27$129
This JetBlue deal was found by Cheapflights users on 11/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/214:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Sun 12/287:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 11/27$131
This JetBlue deal was found by Cheapflights users on 11/28. 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.
Sun 12/148:30 amBOS - ORD
Nonstop3h 05mJetBlue
Sun 1/257:45 amORD - BOS
Nonstop2h 25mJetBlue
Deal found 11/28$132
This JetBlue deal was found by Cheapflights users on 11/28. 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.
Mon 12/155:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Tue 1/610:55 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 11/28$137
This JetBlue deal was found by Cheapflights users on 11/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:30 amBOS - ORD
Nonstop3h 05mJetBlue
Mon 1/57:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 11/27$138
This United Airlines deal was found by Cheapflights users on 11/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Wed 12/176:17 pmORD - BOS
Nonstop2h 28mUnited Airlines
Deal found 11/27$144
This Kissandfly.com deal was found by Cheapflights users on 11/26. 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.
Thu 12/116:00 amBOS - ORD
Nonstop3h 00mJetBlue
Thu 12/1111:25 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 11/26$145
This Delta deal was found by Cheapflights users on 11/28. 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 12/1712:50 pmBOS - ORD
Nonstop2h 57mDelta
Mon 1/125:00 pmORD - BOS
Nonstop2h 21mDelta
Deal found 11/28$147
This Trip.com deal was found by Cheapflights users on 11/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/148:30 amBOS - ORD
Nonstop3h 05mJetBlue
Sat 1/248:45 amORD - BOS
1 stop5h 30mJetBlue
Deal found 11/28$149
This American Airlines deal was found by Cheapflights users on 11/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Fri 12/128:02 pmORD - BOS
Nonstop2h 38mAmerican Airlines
Deal found 11/29$152
This United Airlines deal was found by Cheapflights users on 11/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Fri 12/121:55 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 11/27$154

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 29, 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

Sun 12/14

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Wed 1/21

7:45 am-11:10 am

Nonstop2h 25m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/20

6:00 am-8:05 am

Nonstop3h 05m

Chicago O'Hare Intl

Sun 4/5

7:10 am-10:33 am

Nonstop2h 23m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/5

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 2/9

7:45 am-11:10 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/16

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Tue 1/6

10:55 am-2:19 pm

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/18

9:15 am-3:34 pm

1 stop5h 19m

$142

HartfordMilwaukee

BDL - MKE

BDLMKE

Hartford Bradley Intl

Fri 1/9

8:34 pm-7:14 pm

1 stop23h 40m

Milwaukee-Mitchell

Sun 1/11

7:40 pm-7:24 pm

1 stop22h 44m

$146

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 2/23

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Tue 3/3

10:00 am-1:23 pm

Nonstop2h 23m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/4

1:40 pm-7:36 pm

1 stop6h 56m

Chicago O'Hare Intl

Wed 2/11

6:00 pm-9:29 pm

Nonstop2h 29m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/24

1:40 pm-7:36 pm

1 stop6h 56m

Chicago O'Hare Intl

Sun 1/25

7:45 am-11:10 am

Nonstop2h 25m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/7

12:15 pm-7:36 pm

1 stop8h 21m

Chicago O'Hare Intl

Sun 1/11

7:45 am-11:10 am

Nonstop2h 25m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/28

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 29, 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. Thursday evenings 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 29, 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
4,255 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,255 reviews
Southwest
8.0
Very good
4,255 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,012 reviews
Southwest
8.0
Very good
4,255 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,058 reviews
Southwest
8.0
Very good
4,255 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,044 reviews
Southwest
8.0
Very good
4,255 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
JetBlue
7.2
Good
2,904 reviews
Southwest
8.0
Very good
4,255 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 08m. Delta provides one of the quickest options available for as low as $120. 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 United Airlines ($64), JetBlue ($64), and Southwest ($104).

  • 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$115Average$296FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$145Average$187FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$280FlexibilityNo cancel feeOn-time63%
DeltaCheapest$184Average$462FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$439FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$202Average$438FlexibilityNo cancel feeOn-time69%

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