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$74+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
abr. 6 — abr. 131
dom. 4/6
dom. 4/13
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 abril 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(JetBlue Airways)

One-way from

$74
(Southwest)

Popular in

December

Cheapest in

August

Average price

$318

Good round-trip deal

$238 or less

Good one-way deal

$128 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. 14% potential increase in price ($59 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 April 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 abril 1, 2025.

This JetBlue Airways deal was found by Cheapflights users on 3/31. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/285:15 pmBOS - ORD
Nonstop3h 12mJetBlue
vie. 5/26:30 pmORD - BOS
Nonstop2h 39mJetBlue
Deal found 3/31$132
This United Airlines deal was found by Cheapflights users on 3/31. 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.
sáb. 4/266:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
sáb. 5/312:50 pmORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 3/31$134
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/265:45 pmBOS - ORD
1 stop8h 13mSpirit Airlines
mié. 4/307:47 pmORD - BOS
1 stop13h 35mSpirit Airlines
Deal found 4/1$135
This American Airlines deal was found by Cheapflights users on 3/31. 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.
mar. 4/82:18 pmORH - ORD
1 stop21h 47mAmerican Airlines
jue. 4/105:10 pmORD - ORH
1 stop19h 15mAmerican Airlines
Deal found 3/31$154
This Priceline deal was found by Cheapflights users on 3/31. 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.
mar. 4/292:12 pmBOS - ORD
1 stop11h 08mMultiple Airlines
jue. 5/14:15 pmORD - BOS
1 stop7h 50mMultiple Airlines
Deal found 3/31$164
This Delta deal was found by Cheapflights users on 3/31. 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.
sáb. 4/267:25 pmBOS - ORD
Nonstop2h 57mDelta
vie. 5/27:20 pmORD - BOS
Nonstop2h 26mDelta
Deal found 3/31$177
This American Airlines deal was found by Cheapflights users on 4/1. 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.
jue. 4/106:10 amBOS - ORD
Nonstop3h 08mAmerican Airlines
mar. 4/158:05 amORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 4/1$178
This JetBlue deal was found by Cheapflights users on 3/31. 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.
mar. 6/32:08 pmBOS - MKE
Nonstop2h 40mJetBlue
sáb. 6/75:40 pmMKE - BOS
Nonstop2h 17mJetBlue
Deal found 3/31$187
This Booking.com deal was found by Cheapflights users on 3/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/87:47 pmBOS - MKE
1 stop12h 56mSpirit Airlines
lun. 5/1212:22 pmMKE - BOS
1 stop10h 25mSpirit Airlines
Deal found 3/31$189
This Southwest deal was found by Cheapflights users on 4/1. 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.
dom. 5/46:40 amBOS - ORD
1 stop8h 25mSouthwest
mié. 5/71:50 pmORD - BOS
1 stop6h 15mSouthwest
Deal found 4/1$196
This United Airlines deal was found by Cheapflights users on 3/31. 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.
mié. 4/309:45 amBOS - MKE
2 stops7h 57mUnited Airlines
sáb. 5/31:10 pmMKE - BOS
1 stop5h 38mUnited Airlines
Deal found 3/31$202
This Mytrip deal was found by Cheapflights users on 3/31. 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.
vie. 5/96:00 amBOS - MSP
2 stops17h 00mMultiple Airlines
dom. 5/116:54 amMSP - BOS
Nonstop2h 48mMultiple Airlines
Deal found 3/31$206

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 abril 1, 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

lun. 4/28

5:15 pm-7:27 pm

Nonstop3h 12m

Chicago O'Hare Intl

vie. 5/2

6:30 pm-10:09 pm

Nonstop2h 39m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 4/26

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

sáb. 5/3

12:50 pm-4:17 pm

Nonstop2h 27m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 4/26

5:45 pm-12:58 am

1 stop8h 13m

Chicago O'Hare Intl

mié. 4/30

7:47 pm-10:22 am

1 stop13h 35m

$135

WorcesterChicago

ORH - ORD

ORHORD

Worcester

lun. 6/30

1:49 pm-9:16 am

1 stop20h 27m

Chicago O'Hare Intl

vie. 7/4

4:59 pm-12:43 pm

1 stop18h 44m

$154

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 4/29

2:12 pm-12:20 am

1 stop11h 08m

Chicago O'Hare Intl

jue. 5/1

4:15 pm-1:05 am

1 stop7h 50m

$164

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 4/10

6:10 am-8:18 am

Nonstop3h 08m

Chicago O'Hare Intl

mar. 4/15

8:05 am-11:30 am

Nonstop2h 25m

$178

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

mar. 6/3

2:08 pm-3:48 pm

Nonstop2h 40m

Milwaukee-Mitchell

sáb. 6/7

5:40 pm-8:57 pm

Nonstop2h 17m

$187

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

jue. 5/8

7:47 pm-7:43 am

1 stop12h 56m

Milwaukee-Mitchell

lun. 5/12

12:22 pm-11:47 pm

1 stop10h 25m

$189

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

dom. 5/4

6:40 am-2:05 pm

1 stop8h 25m

Chicago O'Hare Intl

mié. 5/7

1:50 pm-9:05 pm

1 stop6h 15m

$196

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

mié. 4/30

9:45 am-4:42 pm

2 stops7h 57m

Milwaukee-Mitchell

sáb. 5/3

1:10 pm-7:48 pm

1 stop5h 38m

$202

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 abril 1, 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 abril 1, 2025.
See what other customers who have flown with Alaska Airlines, Southwest 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.
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,823 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,275 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,899 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,615 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,823 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Southwest ($74), United Airlines ($77), and Sun Country Air ($78).

  • 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 abril 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$172FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$160Average$319FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$176Average$479FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$447FlexibilityNo cancel feeOn-time69%
DeltaCheapest$194Average$556FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$247Average$388FlexibilityNo cancel feeOn-time63%

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