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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
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

Keep the following information in mind while searching for Massachusetts to Wisconsin flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$126
(Cheapflightsfares)

One-way from

$64
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$270

Good round-trip deal

$192 or less

Good one-way deal

$158 or less
From Massachusetts to Wisconsin
Search Deals
One-way flight from Massachusetts to Wisconsin
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

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 septiembre 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
mié. 10/156:16 amBOS - ORD
1 stop13h 22mSpirit Airlines
mar. 10/216:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/14$126
This Priceline deal was found by Cheapflights users on 9/14. 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.
mar. 9/307:00 amBOS - ORD
Nonstop2h 56mJetBlue
mié. 10/17:50 pmORD - BOS
Nonstop2h 35mJetBlue
Deal found 9/14$127
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
mié. 10/153:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
sáb. 10/1811:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Deal found 9/14$129
This Priceline deal was found by Cheapflights users on 9/14. 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.
sáb. 10/48:38 amBOS - ORD
1 stop9h 07mMultiple Airlines
mar. 10/76:00 amORD - BOS
1 stop6h 20mMultiple Airlines
Deal found 9/14$131
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/264:40 pmBOS - ORD
Nonstop3h 15mJetBlue
vie. 10/37:50 pmORD - BOS
Nonstop2h 35mJetBlue
Deal found 9/15$132
This United Airlines deal was found by Cheapflights users on 9/15. 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.
sáb. 10/186:00 amBOS - ORD
Nonstop2h 56mUnited Airlines
dom. 10/196:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 9/15$133
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/157:09 amBOS - ORD
Nonstop3h 13mJetBlue
mié. 10/157:13 pmORD - BOS
Nonstop2h 33mJetBlue
Deal found 9/15$135
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
mié. 10/83:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
sáb. 10/1111:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Deal found 9/14$136
This United Airlines deal was found by Cheapflights users on 9/15. 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.
jue. 9/258:00 amBOS - ORD
Nonstop2h 55mUnited Airlines
sáb. 9/277:30 amORD - BOS
Nonstop2h 32mUnited Airlines
Deal found 9/15$137
This American Airlines deal was found by Cheapflights users on 9/14. 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. 9/2411:28 amBOS - ORD
Nonstop2h 56mAmerican Airlines
dom. 9/286:05 amORD - BOS
Nonstop2h 27mAmerican Airlines
Deal found 9/14$138
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/68:24 pmBOS - ORD
1 stop23h 14mSpirit Airlines
mié. 10/86:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/15$139
This United Airlines deal was found by Cheapflights users on 9/16. 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.
dom. 9/286:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
mar. 10/217:30 amORD - BOS
Nonstop2h 32mUnited Airlines
Deal found 9/16$140

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 septiembre 16, 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

sáb. 10/18

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

dom. 10/19

6:30 am-9:56 am

Nonstop2h 26m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 10/18

5:05 am-11:50 am

1 stop7h 45m

Chicago O'Hare Intl

mié. 10/22

1:50 pm-9:10 pm

1 stop6h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 11/20

10:40 am-12:40 pm

Nonstop3h 00m

Chicago O'Hare Intl

mié. 11/26

9:25 pm-12:45 am

Nonstop2h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 9/26

4:40 pm-6:55 pm

Nonstop3h 15m

Chicago O'Hare Intl

sáb. 9/27

9:51 am-1:20 pm

Nonstop2h 29m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 12/11

7:50 pm-9:46 pm

Nonstop2h 56m

Chicago O'Hare Intl

dom. 12/14

7:10 am-10:37 am

Nonstop2h 27m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 10/22

5:30 am-12:45 pm

2 stops8h 15m

Chicago O'Hare Intl

sáb. 10/25

12:40 pm-10:15 pm

2 stops8h 35m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 10/23

7:15 am-12:45 pm

1 stop6h 30m

Chicago O'Hare Intl

lun. 10/27

2:50 pm-8:25 am

2 stops16h 35m

$153

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 10/4

8:00 am-9:55 am

Nonstop2h 55m

Chicago O'Hare Intl

mar. 10/7

11:45 am-5:54 pm

1 stop5h 09m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 10/24

8:47 pm-10:35 pm

Nonstop2h 48m

Chicago O'Hare Intl

sáb. 10/25

10:41 am-4:22 pm

1 stop4h 41m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 10/18

6:15 pm-8:09 pm

Nonstop2h 54m

Chicago O'Hare Intl

mié. 10/22

7:10 am-1:25 pm

1 stop5h 15m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, 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 septiembre 16, 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.

Weekly flight availability from Massachusetts to Wisconsin

Explore weekly flight availability from Massachusetts to Wisconsin. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated septiembre 16, 2025.

The most flights from USMA to USWI are scheduled on a Friday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 septiembre 16, 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
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,914 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 2h 56m. United Airlines provides one of the quickest options available for as low as $133. 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 Delta ($69), Southwest ($69), and JetBlue ($69).

  • 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.

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.
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Miami flights
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to Las Vegas flights
San Francisco to John F Kennedy Intl flights
Los Angeles to Seattle flights
LaGuardia to Dallas/Fort Worth flights
Dallas/Fort Worth to Seattle flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to O'Hare Intl flights
Los Angeles to Newark flights
O'Hare Intl to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
Newark to Las Vegas flights
LaGuardia to O'Hare Intl flights
LaGuardia to Fort Lauderdale flights
Seattle to Las Vegas flights
O'Hare Intl to Las Vegas flights
Newark to O'Hare Intl flights
O'Hare Intl to LaGuardia flights
Newark to Miami flights
San Francisco to Las Vegas flights
John F Kennedy Intl to Atlanta flights
John F Kennedy Intl to Orlando flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Dallas/Fort Worth flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to San Francisco flights
Seattle to Dallas/Fort Worth flights
Seattle to Los Angeles flights
Newark to Los Angeles flights
Dallas/Fort Worth to Denver flights
LaGuardia to Miami flights
Los Angeles to Honolulu flights
Los Angeles to Dallas/Fort Worth flights
Los Angeles to LaGuardia flights
O'Hare Intl to Dallas/Fort Worth flights
San Francisco to Newark flights
Newark to Orlando flights
O'Hare Intl to Newark flights
Atlanta to John F Kennedy Intl flights
Dallas/Fort Worth to Los Angeles flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Sky Harbor Intl flights
Dulles Intl to Dallas/Fort Worth flights
Atlanta to Las Vegas flights

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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$112Average$187FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$117Average$297FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$303FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$468FlexibilityNo cancel feeOn-time69%
DeltaCheapest$190Average$491FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$455FlexibilityNo cancel feeOn-time71%

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.