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$63+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
janv. 17 — janv. 241
sam. 1/17
sam. 1/24
1 adult, Economy
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Cheap 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 décembre 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/17. 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.
mer. 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
jeu. 1/14:15 pmBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/17$127
This United Airlines deal was found by Cheapflights users on 12/17. 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.
mer. 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
lun. 1/56:23 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 12/17$132
This JetBlue deal was found by Cheapflights users on 12/17. 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.
sam. 12/278:15 pmORD - BOS
Nonstop2h 29mJetBlue
dim. 12/284:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17$137
This JetBlue deal was found by Cheapflights users on 12/17. 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.
dim. 12/287:41 pmORD - BOS
Nonstop2h 29mJetBlue
mar. 12/304:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17$147
This Priceline deal was found by Cheapflights users on 12/17. 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.
mer. 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
jeu. 1/14:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/17$157
This United Airlines deal was found by Cheapflights users on 12/15. 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.
dim. 12/219:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
jeu. 1/86:21 pmBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 12/15$158
This United Airlines deal was found by Cheapflights users on 12/17. 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.
mer. 12/316:21 pmORD - BOS
1 stop4h 33mUnited Airlines
jeu. 1/16:29 pmBOS - ORD
Nonstop3h 06mUnited Airlines
Deal found 12/17$162
This United Airlines deal was found by Cheapflights users on 12/17. 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.
mer. 12/316:21 pmORD - BOS
1 stop4h 33mUnited Airlines
lun. 1/56:23 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 12/17$167
This United Airlines deal was found by Cheapflights users on 12/15. 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.
mer. 12/246:21 pmORD - BDL
1 stop4h 37mUnited Airlines
jeu. 1/16:15 pmBDL - ORD
Nonstop3h 02mUnited Airlines
Deal found 12/15$167
This Delta deal was found by Cheapflights users on 12/16. 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.
ven. 12/197:10 amORD - BOS
Nonstop2h 26mDelta
mar. 1/137:55 pmBOS - ORD
Nonstop3h 06mDelta
Deal found 12/16$177
This Delta deal was found by Cheapflights users on 12/16. 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.
mer. 12/246:45 amORD - BDL
1 stop7h 57mDelta
jeu. 1/14:47 pmBDL - ORD
1 stop8h 15mDelta
Deal found 12/16$177
This United Airlines deal was found by Cheapflights users on 12/16. 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.
mer. 12/246:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
mer. 12/3112:20 pmBOS - ORD
Nonstop3h 03mUnited Airlines
Deal found 12/16$179

Find flight deals from Wisconsin to Massachusetts

Keep the following information in mind while searching for Wisconsin to Massachusetts flight deals. Data was last updated décembre 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$124
(Kiwi.com)

One-way from

$63
(Super.com)

Popular in

January

Cheapest in

September

Average price

$478

Good round-trip deal

$339 or less

Good one-way deal

$198 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
Search Deals
From Wisconsin to Massachusetts
Search Deals
One-way flight from Wisconsin to Massachusetts
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($100 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Wisconsin to Massachusetts.
Search Deals
Price to beat on a one-way flight from Wisconsin to Massachusetts.
Search Deals

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 décembre 18, 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

sam. 1/17

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

mar. 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sam. 1/17

5:15 am-4:28 pm

1 stop10h 13m

Boston Logan Intl

mar. 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mer. 1/7

5:00 pm-8:21 pm

Nonstop2h 21m

Boston Logan Intl

dim. 1/11

7:55 pm-10:01 pm

Nonstop3h 06m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

ven. 1/9

7:30 am-10:52 am

Nonstop2h 22m

Boston Logan Intl

dim. 1/11

10:30 am-12:34 pm

Nonstop3h 04m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sam. 4/18

6:26 pm-9:51 pm

Nonstop2h 25m

Boston Logan Intl

mer. 4/22

3:39 pm-5:31 pm

Nonstop2h 52m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sam. 1/10

2:00 pm-5:29 pm

Nonstop2h 29m

Boston Logan Intl

dim. 1/11

7:55 pm-10:01 pm

Nonstop3h 06m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

lun. 1/12

7:30 am-10:52 am

Nonstop2h 22m

Boston Logan Intl

mer. 1/14

4:16 pm-6:16 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mer. 1/7

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

mer. 1/14

3:35 pm-5:43 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sam. 1/24

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

dim. 1/25

7:30 am-9:41 am

Nonstop3h 11m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

ven. 5/15

8:21 pm-11:56 pm

Nonstop2h 35m

Boston Logan Intl

dim. 5/17

6:00 am-7:55 am

Nonstop2h 55m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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, September is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $93). Flying from Wisconsin to Massachusetts in January is currently the most expensive (average of $230). 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 décembre 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Wisconsin to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 57% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Wisconsin to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to Massachusetts flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 décembre 18, 2025.
Read through reviews of airlines operating flights from Wisconsin to Massachusetts, such as Southwest, Delta, and United Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,055 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,897 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How popular is this Wisconsin to Massachusetts flight route?

    Within the past month, 7 users have taken a look at flights from Wisconsin to Massachusetts.

  • How long is the flight from Wisconsin to Massachusetts?

    For as low as $137, JetBlue can have you in Massachusetts from Wisconsin in 2h 21m. Airlines will cover a distance of 864 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Wisconsin to Massachusetts one-way?

    $78 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $93 and $98, 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, September is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $93). Flying from Wisconsin to Massachusetts in January is currently the most expensive (average of $230). 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 5 airlines flying from Wisconsin to Massachusetts

Discover the top 5 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 décembre 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$280FlexibilityNo cancel feeOn-time62%
DeltaCheapest$150Average$378FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$259FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$418FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$192Average$387FlexibilityNo cancel feeOn-time69%

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