HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$62+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Massachusetts with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$153
(Mytrip)

One-way from

$62
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$286

Good round-trip deal

$276 or less

Good one-way deal

$173 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. 11% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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

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 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.
Wed 3/510:25 amORD - BOS
3 stops33h 55mSpirit Airlines
Wed 3/125:00 pmBOS - ORD
2 stops15h 44mSpirit Airlines
Deal found 2/19$151
This Booking.com 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/13:25 pmORD - BOS
1 stop8h 05mMultiple Airlines
Wed 3/511:14 amBOS - ORD
1 stop13h 42mMultiple Airlines
Deal found 2/19$152
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/57:10 amORD - BOS
Nonstop2h 33mDelta
Sun 3/97:00 amBOS - ORD
Nonstop3h 09mDelta
Deal found 2/20$155
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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.
Sun 6/227:12 amMSP - BDL
Nonstop2h 35mSun Country Air
Fri 6/278:00 pmBDL - MSP
Nonstop3h 02mSun Country Air
Deal found 2/18$155
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/53:13 pmORD - BOS
Nonstop2h 24mAmerican Airlines
Mon 4/78:59 pmBOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 2/20$158
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/274:21 pmORD - BOS
1 stop7h 23mFrontier
Thu 3/275:10 amBOS - ORD
1 stop6h 40mFrontier
Deal found 2/19$162
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/16:30 pmORD - BOS
Nonstop2h 29mJetBlue
Sun 5/46:00 amBOS - ORD
Nonstop3h 01mJetBlue
Deal found 2/19$167
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.
Wed 3/195:30 amMSP - BDL
1 stop5h 15mAmerican Airlines
Wed 3/267:35 amBDL - MSP
1 stop7h 15mAmerican Airlines
Deal found 2/19$167
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.
Thu 4/37:10 amORD - BOS
Nonstop2h 28mUnited Airlines
Sun 4/67:43 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 2/19$168
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Tue 3/46:00 amMSP - BOS
2 stops30h 01mSpirit Airlines
Tue 3/1112:15 pmBOS - MSP
2 stops28h 40mSpirit Airlines
Deal found 2/18$176
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.
Wed 4/211:20 amORD - ALB
Nonstop2h 06mUnited Airlines
Wed 4/96:00 amALB - ORD
Nonstop2h 31mUnited Airlines
Deal found 2/19$177
This Sun Country Air deal was found by Cheapflights users on 2/18. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/48:34 amMSP - BOS
Nonstop2h 55mSun Country Air
Wed 4/911:38 amBOS - MSP
Nonstop3h 13mSun Country Air
Deal found 2/18$178

Find flights from Wisconsin to Massachusetts within your budget

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 February 20, 2025.

Fly from

Wisconsin

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 3/5

10:25 am-9:20 pm

3 stops33h 55m

Boston Logan Intl

Wed 3/12

5:00 pm-7:44 am

2 stops15h 44m

$151

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/17

9:20 am-12:47 am

1 stop14h 27m

Boston Logan Intl

Mon 4/21

9:31 pm-8:04 am

1 stop11h 33m

$153

MinneapolisHartford

MSP - BDL

MSPBDL

Minneapolis St Paul

Sun 6/22

7:12 am-10:47 am

Nonstop2h 35m

Hartford Bradley Intl

Fri 6/27

8:00 pm-10:02 pm

Nonstop3h 02m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/7

7:10 am-10:43 am

Nonstop2h 33m

Boston Logan Intl

Mon 3/10

7:25 am-9:34 am

Nonstop3h 09m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 4/5

3:13 pm-6:37 pm

Nonstop2h 24m

Boston Logan Intl

Mon 4/7

8:59 pm-10:57 pm

Nonstop2h 58m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 3/9

8:10 am-9:11 am

1 stop24h 01m

Boston Logan Intl

Sun 3/16

6:00 am-7:44 am

1 stop26h 44m

$162

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 3/6

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

Mon 3/10

5:30 am-9:35 am

1 stop5h 05m

$164

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/1

6:30 pm-9:59 pm

Nonstop2h 29m

Boston Logan Intl

Sun 5/4

6:00 am-8:01 am

Nonstop3h 01m

$167

MinneapolisHartford

MSP - BDL

MSPBDL

Minneapolis St Paul

Wed 3/19

5:30 am-11:45 am

1 stop5h 15m

Hartford Bradley Intl

Wed 3/26

7:35 am-1:50 pm

1 stop7h 15m

$167

MinneapolisBoston

MSP - BOS

MSPBOS

Minneapolis St Paul

Tue 3/4

6:00 am-1:01 pm

2 stops30h 01m

Boston Logan Intl

Tue 3/11

12:15 pm-3:55 pm

2 stops28h 40m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 60 results
1
2
3
...
6

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.

Travel insights for flights from Wisconsin to Massachusetts

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

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 $311). 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 February 20, 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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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 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?

    $62 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Spirit Airlines and JetBlue, with prices starting from $78 and $79, 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 $311). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Los Angeles flights
Newark to Orlando flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Las Vegas flights
Newark to Los Angeles flights
John F Kennedy Intl to Orlando flights
Los Angeles to Newark flights
John F Kennedy Intl to West Palm Beach flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Dallas/Fort Worth flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Las Vegas flights
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to LaGuardia flights
LaGuardia to Orlando flights
Dallas/Fort Worth to Seattle flights
San Francisco to John F Kennedy Intl flights
Dallas/Fort Worth to Las Vegas flights
Newark to Las Vegas flights
Newark to Tampa flights
Boston to Fort Lauderdale flights
Seattle to Los Angeles flights
Newark to Dallas/Fort Worth flights
Dallas/Fort Worth to Orlando flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Miami flights
Seattle to Sky Harbor Intl flights
O'Hare Intl to Sky Harbor Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
John F Kennedy Intl to San Francisco flights
LaGuardia to Tampa flights
John F Kennedy Intl to Sky Harbor Intl flights
John F Kennedy Intl to Tampa flights
Reagan-National to Miami flights
Minneapolis to Sky Harbor Intl flights
Dulles Intl to Orlando flights
Seattle to Las Vegas flights
Minneapolis to Las Vegas flights
Los Angeles to Seattle flights
John F Kennedy Intl to Atlanta flights
Dallas/Fort Worth to Newark flights
San Francisco to Newark flights
Dulles Intl to Dallas/Fort Worth flights
Boston to Miami flights

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$34Average$267FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$151Average$291FlexibilityNo cancel feeOn-time62%
DeltaCheapest$161Average$451FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$440FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$447FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$211Average$378FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.