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$55+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$151
(Mytrip)

One-way from

$55
(Frontier)

Popular in

December

Cheapest in

March

Average price

$331

Good round-trip deal

$285 or less

Good one-way deal

$163 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. 16% potential increase in price ($68 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 February 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 February 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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.
Thu 4/242:12 pmBOS - ORD
3 stops18h 52mSpirit Airlines
Mon 4/2810:19 amORD - BOS
2 stops27h 36mSpirit Airlines
Deal found 2/19$151
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/216:00 amBOS - ORD
1 stop12h 26mFrontier
Mon 3/245:47 pmORD - BOS
1 stop5h 57mFrontier
Deal found 2/20$152
This FlightHub deal was found by Cheapflights users on 2/19. 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 4/108:31 pmBOS - ORD
1 stop12h 33mMultiple Airlines
Mon 4/148:55 amORD - BOS
1 stop14h 52mMultiple Airlines
Deal found 2/19$153
This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/278:00 pmBDL - MSP
Nonstop3h 02mSun Country Air
Sun 7/67:12 amMSP - BDL
Nonstop2h 35mSun Country Air
Deal found 2/19$155
This Delta deal was found by Cheapflights users on 2/20. 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 2/277:15 amBOS - ORD
Nonstop3h 06mDelta
Fri 2/287:10 amORD - BOS
Nonstop2h 33mDelta
Deal found 2/20$157
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Thu 3/612:02 pmBDL - MKE
1 stop25h 17mFrontier
Mon 3/101:19 pmMKE - BDL
1 stop20h 43mFrontier
Deal found 2/19$160
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/48:59 pmBOS - ORD
Nonstop2h 58mAmerican Airlines
Mon 4/76:35 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 2/19$161
This United Airlines deal was found by Cheapflights users on 2/19. 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.
Sat 3/85:30 amBOS - ORD
1 stop5h 08mUnited Airlines
Wed 3/124:05 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 2/19$163
This American Airlines deal was found by Cheapflights users on 2/19. 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 3/147:08 pmBDL - MSP
1 stop5h 48mAmerican Airlines
Sat 3/155:42 pmMSP - BDL
1 stop6h 08mAmerican Airlines
Deal found 2/19$167
This JetBlue deal was found by Cheapflights users on 2/20. 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.
Fri 3/75:37 amBOS - ORD
1 stop6h 22mJetBlue
Thu 3/131:15 pmORD - BOS
Nonstop2h 24mJetBlue
Deal found 2/20$177
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Fri 3/219:13 amBOS - MSN
1 stop9h 26mFrontier
Fri 3/286:29 pmMSN - BOS
1 stop29h 15mFrontier
Deal found 2/20$178
This FlightHub deal was found by Cheapflights users on 2/20. 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 3/135:07 pmBOS - MSP
1 stop7h 52mSpirit Airlines
Mon 3/173:20 pmMSP - BOS
1 stop16h 32mSpirit Airlines
Deal found 2/20$179

Find flights from Massachusetts to Wisconsin within your budget

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 February 20, 2025.

Fly from

Massachusetts

Fly to

Wisconsin

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/24

2:12 pm-8:04 am

3 stops18h 52m

Chicago O'Hare Intl

Mon 4/28

10:19 am-2:55 pm

2 stops27h 36m

$151

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/21

6:00 am-5:26 pm

1 stop12h 26m

Chicago O'Hare Intl

Mon 3/24

5:47 pm-12:44 am

1 stop5h 57m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/10

8:31 pm-8:04 am

1 stop12h 33m

Chicago O'Hare Intl

Mon 4/14

8:55 am-12:47 am

1 stop14h 52m

$153

HartfordMinneapolis

BDL - MSP

BDLMSP

Hartford Bradley Intl

Fri 6/27

8:00 pm-10:02 pm

Nonstop3h 02m

Minneapolis St Paul

Sun 7/6

7:12 am-10:47 am

Nonstop2h 35m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/4

7:15 am-9:21 am

Nonstop3h 06m

Chicago O'Hare Intl

Wed 3/5

7:10 am-10:43 am

Nonstop2h 33m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 3/15

7:30 am-9:34 am

Nonstop3h 04m

Chicago O'Hare Intl

Tue 3/18

7:30 am-10:49 am

Nonstop2h 19m

$158

HartfordMilwaukee

BDL - MKE

BDLMKE

Hartford Bradley Intl

Thu 3/6

12:02 pm-12:19 pm

1 stop25h 17m

Milwaukee-Mitchell

Mon 3/10

1:19 pm-11:02 am

1 stop20h 43m

$160

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/4

8:59 pm-10:57 pm

Nonstop2h 58m

Chicago O'Hare Intl

Mon 4/7

6:35 pm-10:06 pm

Nonstop2h 31m

$161

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/7

6:00 am-8:01 am

Nonstop3h 01m

Chicago O'Hare Intl

Fri 5/9

1:12 pm-6:38 pm

1 stop4h 26m

$167

HartfordMinneapolis

BDL - MSP

BDLMSP

Hartford Bradley Intl

Fri 3/14

7:08 pm-11:56 pm

1 stop5h 48m

Minneapolis St Paul

Sat 3/15

5:42 pm-12:50 am

1 stop6h 08m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Massachusetts to Wisconsin

Get recent, data-driven insights about flights from Massachusetts to Wisconsin including ideal travel times, pricing trends, and more.

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 February 20, 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.

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 February 20, 2025.
See what other customers who have flown with Southwest, Alaska Airlines and Delta from Massachusetts to Wisconsin have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Frontier ($55), Spirit Airlines ($70), and Sun Country Air ($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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$171FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$152Average$307FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$175Average$490FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$537FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$186Average$468FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$226Average$395FlexibilityNo cancel feeOn-time63%
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