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$59+ Cheap flights from Wisconsin to Massachusetts

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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
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Cheap flight deals from Wisconsin to Massachusetts

Keep the following information in mind while searching for Wisconsin to Massachusetts flight deals. Data was last updated mayo 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$116
(Cheapflightsfares)

One-way from

$59
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$296

Good round-trip deal

$208 or less

Good one-way deal

$123 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
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From Wisconsin to Massachusetts
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One-way flight from Wisconsin to Massachusetts
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Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Wisconsin to Massachusetts.
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Price to beat on a one-way flight from Wisconsin to Massachusetts.
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Find flight deals from Wisconsin to Massachusetts

Cheapest flights from Wisconsin to Massachusetts
Explore the most affordable flight options available from Wisconsin to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on mayo 1, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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.
jue. 10/1610:48 amORD - BOS
Nonstop2h 26mSpirit Airlines
mar. 10/216:10 amBOS - ORD
1 stop12h 27mSpirit Airlines
Deal found 4/30$113
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/710:50 amORD - BOS
Nonstop2h 28mJetBlue
dom. 5/116:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 4/29$117
This American Airlines deal was found by Cheapflights users on 4/30. 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.
mié. 6/48:20 pmORD - BOS
Nonstop2h 24mAmerican Airlines
mié. 6/115:00 amBOS - ORD
Nonstop2h 54mAmerican Airlines
Deal found 4/30$118
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.
mar. 6/37:53 pmORD - BOS
Nonstop2h 27mUnited Airlines
mar. 8/126:59 pmBOS - ORD
1 stop5h 38mUnited Airlines
Deal found 4/29$123
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.
jue. 5/87:00 amORD - BOS
Nonstop2h 25mDelta
mar. 5/137:15 amBOS - ORD
Nonstop2h 54mDelta
Deal found 4/29$137
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/281:50 pmORD - BOS
1 stop4h 20mSouthwest
vie. 5/305:00 amBOS - ORD
1 stop8h 45mSouthwest
Deal found 4/29$142
This Mytrip deal was found by Cheapflights users on 4/30. 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.
sáb. 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
mié. 5/213:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Deal found 4/30$166
This JetBlue deal was found by Cheapflights users on 4/30. 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.
vie. 5/304:43 pmMKE - BOS
Nonstop2h 16mJetBlue
mar. 6/32:08 pmBOS - MKE
Nonstop2h 40mJetBlue
Deal found 4/30$187
This JetBlue deal was found by Cheapflights users on 4/30. 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.
sáb. 7/56:15 amORD - ACK
1 stop4h 38mJetBlue
mié. 7/94:34 pmACK - ORD
1 stop7h 51mJetBlue
Deal found 4/30$190
This American Airlines deal was found by Cheapflights users on 4/30. 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.
mié. 5/217:07 amMKE - BOS
1 stop5h 46mAmerican Airlines
sáb. 5/316:36 pmBOS - MKE
1 stop6h 22mAmerican Airlines
Deal found 4/30$197
This Booking.com deal was found by Cheapflights users on 4/30. 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.
vie. 5/309:15 amMKE - BOS
1 stop12h 36mSpirit Airlines
mar. 6/35:45 amBOS - MKE
1 stop6h 42mSpirit Airlines
Deal found 4/30$202
This Delta deal was found by Cheapflights users on 4/30. 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.
mié. 6/256:00 amORD - ACK
1 stop4h 25mDelta
mar. 7/14:45 pmACK - ORD
1 stop6h 36mDelta
Deal found 4/30$206

Cheapflights Fare Finder

Customize your flight search to find flights from Wisconsin to Massachusetts 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 mayo 1, 2025.
Use the filters below to find and compare flights from Wisconsin to Massachusetts that are best for you.

Fly from

Wisconsin

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 10/16

10:48 am-2:14 pm

Nonstop2h 26m

Boston Logan Intl

mar. 10/21

6:10 am-5:37 pm

1 stop12h 27m

$113

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 5/10

4:20 pm-7:48 pm

Nonstop2h 28m

Boston Logan Intl

mar. 5/13

12:15 pm-2:12 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 6/4

8:20 pm-11:44 pm

Nonstop2h 24m

Boston Logan Intl

mié. 6/11

5:00 am-6:54 am

Nonstop2h 54m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 5/31

7:00 am-10:25 am

Nonstop2h 25m

Boston Logan Intl

lun. 6/9

7:20 am-9:18 am

Nonstop2h 58m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 5/21

4:03 pm-12:17 am

1 stop7h 14m

Boston Logan Intl

dom. 5/25

6:00 am-8:00 am

Nonstop3h 00m

$140

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 5/28

1:50 pm-7:10 pm

1 stop4h 20m

Boston Logan Intl

vie. 5/30

5:00 am-12:45 pm

1 stop8h 45m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 5/17

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

mié. 5/21

3:49 pm-11:04 pm

1 stop8h 15m

$166

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

vie. 5/30

4:43 pm-7:59 pm

Nonstop2h 16m

Boston Logan Intl

mar. 6/3

2:08 pm-3:48 pm

Nonstop2h 40m

$187

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

sáb. 7/5

6:15 am-3:23 pm

1 stop8h 08m

Nantucket Memorial

mié. 7/9

4:34 pm-11:25 pm

1 stop7h 51m

$190

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

mié. 5/21

7:07 am-3:29 pm

1 stop7h 22m

Boston Logan Intl

mié. 8/13

6:19 pm-10:59 pm

1 stop5h 40m

$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 Wisconsin to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Wisconsin 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 Wisconsin to Massachusetts

What is the cheapest month to book a flight from Wisconsin to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $218). Flying from Wisconsin to Massachusetts in July is currently the most expensive (average of $310). 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 WI to MA?

Find hourly flight availability from Wisconsin to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated mayo 1, 2025.

When flying from Wisconsin to Massachusetts, 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 Massachusetts by month

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

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

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

If weather is an important factor for your trip to Massachusetts, 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 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated mayo 1, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Wisconsin to Massachusetts by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.1

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
9,972 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.1

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
4,294 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.1

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
7,934 reviews
Alaska Airlines
8.0
Very good
9,972 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.1

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
9,972 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.1

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
9,972 reviews

Crew

8.5

Entertainment

7.1

Food

7.1

Boarding

8.1

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 Wisconsin to Massachusetts. 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 Wisconsin to Massachusetts one-way?

    $59 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Spirit Airlines and Southwest, with prices starting from $60 and $68, respectively.

  • Can I find deals for flights from Wisconsin to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Massachusetts.

  • Can I find deals for business class flights from Wisconsin to Massachusetts?

    Yes. Cheapflights offers flight deals from Wisconsin to Massachusetts 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 Wisconsin to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $218). Flying from Wisconsin to Massachusetts in July is currently the most expensive (average of $310). 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 Wisconsin to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Wisconsin to Massachusetts

Discover the top 6 airlines that operate flights from Wisconsin to Massachusetts. 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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$34Average$258FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$152Average$292FlexibilityNo cancel feeOn-time62%
DeltaCheapest$163Average$440FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$431FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$446FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$211Average$364FlexibilityNo cancel feeOn-time63%

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