HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Wisconsin

$75+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Wisconsin (USWI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 21, 2024.

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 November 21, 2024.

This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/610:34 amBOS - ORD
1 stop11h 33mMultiple Airlines
Mon 12/910:59 amORD - BOS
1 stop12h 31mMultiple Airlines
Deal found 11/20$124
This Frontier deal was found by Cheapflights users on 11/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/175:45 amBOS - ORD
1 stop11h 48mFrontier
Thu 1/210:15 pmORD - BOS
1 stop8h 18mFrontier
Deal found 11/20$127
This Cheapflightsfares deal was found by Cheapflights users on 11/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/172:18 pmBOS - ORD
1 stop9h 41mSpirit Airlines
Tue 12/241:24 pmORD - BOS
1 stop6h 56mSpirit Airlines
Deal found 11/20$141
This JetBlue deal was found by Cheapflights users on 11/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/56:00 amBOS - ORD
Nonstop3h 05mJetBlue
Mon 12/98:51 amORD - BOS
Nonstop2h 22mJetBlue
Deal found 11/20$157
This Delta deal was found by Cheapflights users on 11/21. 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.
Tue 12/1711:05 amBOS - ORD
Nonstop2h 55mDelta
Tue 12/247:35 amORD - BOS
Nonstop2h 28mDelta
Deal found 11/21$173
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/159:30 amBOS - ORD
Nonstop2h 56mUnited Airlines
Sun 1/59:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 11/20$182
This Trip.com deal was found by Cheapflights users on 11/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/611:37 amBOS - MSP
Nonstop3h 14mSun Country Air
Mon 12/96:54 amMSP - BOS
Nonstop2h 47mSun Country Air
Deal found 11/20$185
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1411:37 amBOS - MSP
Nonstop3h 14mMultiple Airlines
Tue 12/179:15 amMSP - BOS
1 stop10h 39mMultiple Airlines
Deal found 11/20$186
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/149:00 amBOS - MSP
1 stop8h 18mSpirit Airlines
Tue 12/175:23 pmMSP - BOS
2 stops26h 44mSpirit Airlines
Deal found 11/20$187
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Wed 12/45:53 amBOS - ORD
1 stop6h 05mAmerican Airlines
Sat 12/75:40 pmORD - BOS
Nonstop2h 20mAmerican Airlines
Deal found 11/20$207
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/165:50 pmBDL - ORD
3 stops31h 44mMultiple Airlines
Wed 12/1812:09 pmORD - BDL
1 stop9h 33mMultiple Airlines
Deal found 11/20$229
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/96:00 amBDL - MKE
1 stop16h 42mSpirit Airlines
Tue 12/105:00 amMKE - BDL
1 stop16h 02mSpirit Airlines
Deal found 11/20$241

Find flights from Massachusetts to Wisconsin within your budget

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/6

10:34 am-9:07 pm

1 stop11h 33m

Chicago O'Hare Intl

Mon 12/9

10:59 am-12:30 am

1 stop12h 31m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/17

11:46 am-8:45 pm

1 stop9h 59m

Chicago O'Hare Intl

Tue 1/21

2:59 pm-12:39 am

1 stop8h 40m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/17

2:18 pm-10:59 pm

1 stop9h 41m

Chicago O'Hare Intl

Tue 12/24

1:24 pm-9:20 pm

1 stop6h 56m

$141

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/5

7:20 am-9:29 am

Nonstop3h 09m

Chicago O'Hare Intl

Mon 12/9

6:30 am-10:00 am

Nonstop2h 30m

$157

HartfordMilwaukee

BDL - MKE

BDLMKE

Hartford Bradley Intl

Fri 2/7

9:15 am-5:52 pm

1 stop9h 37m

Milwaukee-Mitchell

Sun 2/9

6:52 pm-10:40 am

1 stop14h 48m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/10

8:35 am-3:44 pm

1 stop8h 09m

Chicago O'Hare Intl

Tue 1/14

9:05 am-12:23 pm

Nonstop2h 18m

$166

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 2/2

5:50 pm-10:57 pm

1 stop6h 07m

Chicago O'Hare Intl

Sat 2/8

10:50 am-4:05 pm

1 stop4h 15m

$176

BostonMinneapolis

BOS - MSP

BOSMSP

Boston Logan Intl

Fri 12/6

11:37 am-1:51 pm

Nonstop3h 14m

Minneapolis St Paul

Mon 12/9

6:54 am-10:41 am

Nonstop2h 47m

$185

BostonMinneapolis

BOS - MSP

BOSMSP

Boston Logan Intl

Sat 12/14

11:37 am-1:51 pm

Nonstop3h 14m

Minneapolis St Paul

Tue 12/17

9:15 am-8:54 pm

1 stop10h 39m

$186

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/3

2:41 pm-4:41 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 12/8

7:00 am-10:28 am

Nonstop2h 28m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

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.

Travel insights for flights from Massachusetts to Wisconsin

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

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

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $277). Flying from Massachusetts to Wisconsin in June is currently the most expensive (average of $361). 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 November 21, 2024.

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.

Rainfall in Wisconsin by month

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

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

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

If weather is an important factor for your trip to Wisconsin, 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 21.2 F).

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 November 21, 2024.
See what other customers who have flown with Frontier, Spirit Airlines and JetBlue from Massachusetts to Wisconsin have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,458 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,396 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Food

7.2

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • 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 Frontier ($75), JetBlue ($79), and Spirit Airlines ($82).

  • 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, January is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $277). Flying from Massachusetts to Wisconsin in June is currently the most expensive (average of $361). 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.
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
Newark to Fort Lauderdale flights
Dallas/Fort Worth to LaGuardia flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
John F Kennedy Intl to Orlando flights
Los Angeles to John F Kennedy Intl flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Los Angeles flights
Newark to Los Angeles flights
Los Angeles to Newark flights
Dallas/Fort Worth to John F Kennedy Intl flights
Newark to Orlando flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Fort Lauderdale flights
Dallas/Fort Worth to Newark flights
LaGuardia to Orlando flights
San Francisco to John F Kennedy Intl flights
Miami to LaGuardia flights
Miami to John F Kennedy Intl flights
Fort Lauderdale to LaGuardia flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Atlanta flights
Fort Lauderdale to Newark flights
Atlanta to John F Kennedy Intl flights
Los Angeles to Dallas/Fort Worth flights
John F Kennedy Intl to San Francisco flights
Los Angeles to Honolulu flights
Dallas/Fort Worth to Orlando flights
Seattle to Los Angeles flights
O'Hare Intl to Orlando flights
Dallas/Fort Worth to Las Vegas flights
Boston to Orlando flights
Dallas/Fort Worth to Los Angeles flights
Miami to Newark flights
O'Hare Intl to Miami flights
Los Angeles to LaGuardia flights
Fort Lauderdale to John F Kennedy Intl flights
John F Kennedy Intl to West Palm Beach flights
O'Hare Intl to Dallas/Fort Worth flights
Orlando to John F Kennedy Intl flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Fort Lauderdale flights
San Francisco to Newark flights
LaGuardia to Los Angeles flights
LaGuardia to Atlanta flights
Baltimore to Fort Lauderdale 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$81Average$175FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$141Average$295FlexibilityNo cancel feeOn-time62%
DeltaCheapest$157Average$517FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$166Average$481FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$453FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$226Average$367FlexibilityNo 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.
View all available airlines