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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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$59
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$339

Good round-trip deal

$219 or less

Good one-way deal

$113 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 ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 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 April 30, 2025.

This JetBlue deal was found by Cheapflights users on 4/28. 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.
Fri 5/96:00 amBOS - ORD
Nonstop3h 00mJetBlue
Tue 5/138:45 amORD - BOS
Nonstop2h 28mJetBlue
Deal found 4/28$117
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/88:51 pmBOS - ORD
Nonstop3h 01mAmerican Airlines
Mon 5/128:20 pmORD - BOS
Nonstop2h 24mAmerican Airlines
Deal found 4/28$118
This Flightnetwork deal was found by Cheapflights users on 4/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/43:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Wed 6/1112:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Deal found 4/29$121
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/16:59 pmBOS - ORD
1 stop5h 38mUnited Airlines
Tue 7/87:30 amORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 4/29$123
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/76:45 amBOS - ORD
1 stop9h 15mSouthwest
Tue 6/104:00 pmORD - BOS
1 stop6h 55mSouthwest
Deal found 4/28$136
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/278:20 pmBOS - ORD
Nonstop2h 54mDelta
Sat 5/317:00 amORD - BOS
Nonstop2h 25mDelta
Deal found 4/29$137
This Delta deal was found by Cheapflights users on 4/28. 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 5/215:10 pmBOS - MKE
Nonstop2h 46mDelta
Wed 6/47:40 pmMKE - BOS
Nonstop2h 19mDelta
Deal found 4/28$177
This Booking.com deal was found by Cheapflights users on 4/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1311:40 amBDL - MSP
Nonstop3h 02mMultiple Airlines
Mon 6/167:47 amMSP - BDL
1 stop6h 02mMultiple Airlines
Deal found 4/28$194
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2111:46 amBDL - MSP
Nonstop3h 02mSun Country Air
Thu 7/247:12 amMSP - BDL
Nonstop2h 35mSun Country Air
Deal found 4/28$195
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/145:00 amBOS - MKE
1 stop7h 02mAmerican Airlines
Wed 6/46:23 pmMKE - BOS
1 stop4h 21mAmerican Airlines
Deal found 4/28$197
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/196:56 pmBOS - MKE
1 stop5h 33mUnited Airlines
Wed 8/205:00 amMKE - BOS
1 stop5h 01mUnited Airlines
Deal found 4/29$202
This FlightHub deal was found by Cheapflights users on 4/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:00 amBOS - ORD
1 stop4h 24mMultiple Airlines
Mon 5/124:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Deal found 4/29$220

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 April 30, 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

Fri 5/9

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Tue 5/13

8:45 am-12:13 pm

Nonstop2h 28m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/4

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Wed 6/11

12:41 pm-11:29 pm

1 stop9h 48m

$121

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/1

6:59 pm-11:37 pm

1 stop5h 38m

Chicago O'Hare Intl

Tue 7/8

7:30 am-10:57 am

Nonstop2h 27m

$123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/7

6:45 am-3:00 pm

1 stop9h 15m

Chicago O'Hare Intl

Tue 6/10

4:00 pm-11:55 pm

1 stop6h 55m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/27

8:20 pm-10:14 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sat 5/31

7:00 am-10:25 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/21

6:35 am-8:31 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 5/28

3:20 pm-6:43 pm

Nonstop2h 23m

$141

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Wed 5/21

5:10 pm-6:56 pm

Nonstop2h 46m

Milwaukee-Mitchell

Wed 6/4

7:40 pm-10:59 pm

Nonstop2h 19m

$177

HartfordMinneapolis

BDL - MSP

BDLMSP

Hartford Bradley Intl

Fri 6/13

11:40 am-1:42 pm

Nonstop3h 02m

Minneapolis St Paul

Mon 6/16

7:47 am-2:49 pm

1 stop6h 02m

$194

HartfordMinneapolis

BDL - MSP

BDLMSP

Hartford Bradley Intl

Mon 7/21

11:46 am-1:48 pm

Nonstop3h 02m

Minneapolis St Paul

Thu 7/24

7:12 am-10:47 am

Nonstop2h 35m

$195

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Wed 5/14

5:00 am-11:02 am

1 stop7h 02m

Milwaukee-Mitchell

Wed 6/4

6:23 pm-11:44 pm

1 stop4h 21m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 April 30, 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 April 30, 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
9,961 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 United Airlines ($59), Spirit Airlines ($60), and Southwest ($68).

  • 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.

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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$172FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$151Average$316FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$176Average$457FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$458FlexibilityNo cancel feeOn-time69%
DeltaCheapest$209Average$541FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$226Average$376FlexibilityNo cancel feeOn-time63%

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