HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Wisconsin

$64+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Wisconsin 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 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 December 28, 2025.

This United Airlines deal was found by Cheapflights users on 12/26. 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 12/316:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Mon 1/59:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/26$137
This United Airlines deal was found by Cheapflights users on 12/26. 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 12/3012:20 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Thu 1/16:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/26$149
This United Airlines deal was found by Cheapflights users on 12/27. 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 12/306:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Wed 12/316:11 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/27$157
This American Airlines deal was found by Cheapflights users on 12/27. 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.
Tue 12/306:36 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Thu 1/18:20 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 12/27$177
This United Airlines deal was found by Cheapflights users on 12/27. 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 12/306:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/27$189
This Super.com deal was found by Cheapflights users on 12/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Fri 1/27:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/27$194
This United Airlines deal was found by Cheapflights users on 12/27. 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 12/316:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/27$195
This United Airlines deal was found by Cheapflights users on 12/26. 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 12/306:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Mon 1/59:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/26$196
This Trip.com deal was found by Cheapflights users on 12/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/304:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Wed 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/27$203
This United Airlines deal was found by Cheapflights users on 12/26. 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 12/3112:20 pmBOS - ORD
Nonstop3h 03mUnited Airlines
Tue 1/610:35 amORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 12/26$207
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2711:49 amBOS - MSP
Nonstop3h 11mSun Country Air
Sat 1/36:54 amMSP - BOS
Nonstop2h 57mSun Country Air
Deal found 12/26$263
This Cheapflightsfares deal was found by Cheapflights users on 12/26. 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 12/286:45 amBOS - MSP
Nonstop3h 11mSun Country Air
Thu 1/16:54 amMSP - BOS
Nonstop2h 57mSun Country Air
Deal found 12/26$337

Find flight deals from Massachusetts to Wisconsin

Keep the following information in mind while searching for Massachusetts to Wisconsin flight deals. Data was last updated December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$127
(Delta)

One-way from

$64
(American Airlines)

Popular in

November

Cheapest in

September

Average price

$396

Good round-trip deal

$299 or less

Good one-way deal

$248 or less
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Milwaukee-Mitchell flights.
Search Deals
From Massachusetts to Wisconsin
Search Deals
One-way flight from Massachusetts to Wisconsin
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 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 Massachusetts to Wisconsin.
Search Deals
Price to beat on a one-way flight from Massachusetts to Wisconsin.
Search Deals

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 December 28, 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

Tue 1/20

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 1/23

7:45 am-11:10 am

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 1/18

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Fri 1/30

10:40 am-2:13 pm

Nonstop2h 33m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/21

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 1/23

7:45 am-11:10 am

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/23

8:25 pm-10:29 pm

Nonstop3h 04m

Chicago O'Hare Intl

Wed 1/28

10:40 am-2:13 pm

Nonstop2h 33m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/21

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Tue 2/24

10:00 am-1:20 pm

Nonstop2h 20m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 1/18

5:15 pm-7:26 pm

Nonstop3h 11m

Chicago O'Hare Intl

Thu 1/29

7:05 am-10:40 am

Nonstop2h 35m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 1/18

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Wed 1/28

2:25 pm-5:54 pm

Nonstop2h 29m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/21

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Thu 1/22

7:45 am-11:10 am

Nonstop2h 25m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

5:15 pm-7:26 pm

Nonstop3h 11m

Chicago O'Hare Intl

Wed 1/28

7:05 am-10:40 am

Nonstop2h 35m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/17

5:15 pm-7:26 pm

Nonstop3h 11m

Chicago O'Hare Intl

Fri 1/30

7:05 am-10:40 am

Nonstop2h 35m

$127

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

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

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, September is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $98). Flying from Massachusetts to Wisconsin in February is currently the most expensive (average of $272). 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 December 28, 2025.

When flying from Massachusetts to Wisconsin, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 46% versus a flight in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Wisconsin. Price data was last updated on December 27, 2025.

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

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 December 28, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Massachusetts to Wisconsin by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

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
8.0
Very good
4,256 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

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
8,018 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

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
9,113 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

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
11,072 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

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
2,901 reviews
Southwest
8.0
Very good
4,256 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Comfort

8.0

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 Massachusetts to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Massachusetts to Wisconsin?

    A quick flight from Massachusetts to Wisconsin can take about 3h 08m. JetBlue provides one of the quickest options available for as low as $127. Airlines will cover a distance of 864 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 JetBlue ($78), American Airlines ($88), and Southwest ($98).

  • 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, September is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $98). Flying from Massachusetts to Wisconsin in February is currently the most expensive (average of $272). 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 Massachusetts to Wisconsin

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

Top 5 airlines flying from Massachusetts to Wisconsin

Discover the top 5 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$296FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$279FlexibilityNo cancel feeOn-time63%
DeltaCheapest$183Average$455FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$433FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$202Average$434FlexibilityNo cancel feeOn-time69%

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.