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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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
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 October 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$117
(Delta)

One-way from

$62
(Trip.com)

Popular in

November

Cheapest in

September

Average price

$307

Good round-trip deal

$233 or less

Good one-way deal

$183 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. 12% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 23, 2025.

This JetBlue deal was found by Cheapflights users on 10/21. 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 11/17:00 amBOS - ORD
Nonstop3h 05mJetBlue
Wed 11/1211:20 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 10/21$117
This Delta deal was found by Cheapflights users on 10/21. 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 12/44:05 pmBOS - ORD
Nonstop2h 57mDelta
Mon 12/87:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 10/21$118
This United Airlines deal was found by Cheapflights users on 10/23. 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 12/317:45 amBOS - ORD
Nonstop3h 04mUnited Airlines
Mon 1/56:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 10/23$119
This United Airlines deal was found by Cheapflights users on 10/21. 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 12/256:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Wed 1/79:13 amORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 10/21$120
This Flysmarter deal was found by Cheapflights users on 10/23. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:40 pmBOS - ORD
1 stop7h 12mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 10/23$121
This United Airlines deal was found by Cheapflights users on 10/23. 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 11/207:45 amBOS - ORD
Nonstop3h 00mUnited Airlines
Thu 11/277:15 amORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 10/23$122
This Trip.com deal was found by Cheapflights users on 10/23. 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.
Mon 11/173:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Wed 11/196:45 amORD - BOS
1 stop7h 15mJetBlue
Deal found 10/23$123
This JetBlue deal was found by Cheapflights users on 10/22. 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 11/157:10 amBOS - ORD
Nonstop3h 05mJetBlue
Mon 11/176:45 amORD - BOS
1 stop7h 15mJetBlue
Deal found 10/22$125
This American Airlines deal was found by Cheapflights users on 10/23. 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 12/314:36 pmBOS - ORD
Nonstop3h 27mAmerican Airlines
Sun 1/412:15 amORD - BOS
Nonstop2h 24mAmerican Airlines
Deal found 10/23$126
This United Airlines deal was found by Cheapflights users on 10/22. 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 11/56:00 amBOS - ORD
Nonstop3h 00mUnited Airlines
Sun 11/96:15 amORD - BOS
Nonstop2h 15mUnited Airlines
Deal found 10/22$129
This Southwest deal was found by Cheapflights users on 10/21. 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.
Sat 12/68:50 amBOS - MKE
1 stop8h 00mSouthwest
Thu 12/1811:50 amMKE - BOS
2 stops9h 40mSouthwest
Deal found 10/21$183
This Southwest deal was found by Cheapflights users on 10/21. 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.
Wed 12/105:45 amBOS - MKE
1 stop4h 45mSouthwest
Wed 12/176:00 amMKE - BOS
2 stops9h 35mSouthwest
Deal found 10/21$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 October 23, 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 12/4

1:40 pm-6:43 pm

1 stop6h 03m

Chicago O'Hare Intl

Mon 12/8

3:50 pm-7:14 pm

Nonstop2h 24m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 11/14

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sun 11/16

6:15 am-9:30 am

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/21

11:00 am-1:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Thu 1/22

7:00 am-1:23 pm

1 stop5h 23m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/14

6:00 am-10:22 am

1 stop5h 22m

Chicago O'Hare Intl

Sun 1/18

7:00 am-10:33 am

Nonstop2h 33m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/21

4:20 pm-11:54 pm

1 stop8h 34m

Chicago O'Hare Intl

Mon 1/26

10:10 am-1:40 pm

Nonstop2h 30m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

4:40 pm-8:35 pm

1 stop4h 55m

Chicago O'Hare Intl

Fri 12/12

7:10 pm-10:34 pm

Nonstop2h 24m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

1:40 pm-6:43 pm

1 stop6h 03m

Chicago O'Hare Intl

Sun 12/7

7:10 am-10:36 am

Nonstop2h 26m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/16

6:00 am-10:09 am

1 stop5h 09m

Chicago O'Hare Intl

Sun 1/18

7:00 am-10:33 am

Nonstop2h 33m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

4:05 pm-8:14 pm

1 stop5h 09m

Chicago O'Hare Intl

Tue 1/20

9:13 am-12:46 pm

Nonstop2h 33m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/8

4:10 pm-6:07 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sun 11/9

7:10 am-10:36 am

Nonstop2h 26m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

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 December is currently the most expensive (average of $276). 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 October 23, 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 October 23, 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
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
7,982 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
8,995 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
11,033 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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
2,908 reviews
Southwest
8.0
Very good
4,236 reviews

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Overall

8.0

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. Delta provides one of the quickest options available for as low as $127. 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 ($69), United Airlines ($71), and JetBlue ($73).

  • 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 December is currently the most expensive (average of $276). 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.

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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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$293FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$145Average$187FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$294FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$453FlexibilityNo cancel feeOn-time69%
DeltaCheapest$186Average$486FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$206Average$446FlexibilityNo cancel feeOn-time71%

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