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$68+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Aug 7 — Aug 141
Thu 8/7
Thu 8/14
1 adult, Economy
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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 August 2, 2025.

Round-trip from

$137
(United Airlines)

One-way from

$69
(United Airlines)

Popular in

December

Cheapest in

May

Average price

$267

Good round-trip deal

$175 or less

Good one-way deal

$123 or less
From Wisconsin to Massachusetts
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One-way flight from Wisconsin to Massachusetts
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Highest demand for flights based on searches. 12% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Wisconsin to Massachusetts.
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Price to beat on a one-way flight from Wisconsin to Massachusetts.
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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 August 2, 2025.

This United Airlines deal was found by Cheapflights users on 7/31. 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.
Fri 9/123:48 pmORD - BOS
Nonstop2h 31mUnited Airlines
Sun 9/146:10 amBOS - ORD
Nonstop2h 55mUnited Airlines
Deal found 7/31$137
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Sun 9/146:05 amORD - BOS
Nonstop2h 27mAmerican Airlines
Sun 9/215:00 amBOS - ORD
Nonstop2h 51mAmerican Airlines
Deal found 7/31$138
This Trip.com deal was found by Cheapflights users on 8/1. 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.
Thu 9/117:50 pmORD - BOS
Nonstop2h 35mJetBlue
Mon 9/154:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 8/1$141
This Booking.com deal was found by Cheapflights users on 7/30. 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.
Tue 8/198:12 pmORD - BOS
1 stop14h 06mSpirit Airlines
Tue 8/266:05 amBOS - ORD
1 stop14h 02mSpirit Airlines
Deal found 7/30$145
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 9/410:15 amORD - BOS
Nonstop2h 33mDelta
Wed 9/107:55 pmBOS - ORD
Nonstop3h 01mDelta
Deal found 7/31$147
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/122:55 pmORD - BOS
1 stop6h 40mSouthwest
Mon 9/1510:45 amBOS - ORD
1 stop6h 40mSouthwest
Deal found 7/30$157
This Priceline deal was found by Cheapflights users on 7/31. 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.
Sat 8/305:38 pmMKE - BOS
Nonstop2h 12mJetBlue
Tue 9/21:40 pmBOS - MKE
Nonstop2h 28mJetBlue
Deal found 7/31$157
This Sun Country Air deal was found by Cheapflights users on 7/31. 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.
Thu 8/77:12 amMSP - BDL
Nonstop2h 35mSun Country Air
Mon 8/257:42 pmBDL - MSP
Nonstop3h 06mSun Country Air
Deal found 7/31$158
This CheapOair deal was found by Cheapflights users on 7/30. 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.
Wed 8/208:12 pmORD - BOS
1 stop14h 06mMultiple Airlines
Sun 8/249:20 amBOS - ORD
1 stop10h 21mMultiple Airlines
Deal found 7/30$171
This United Airlines deal was found by Cheapflights users on 8/1. 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 8/318:48 amORD - BDL
Nonstop2h 32mUnited Airlines
Sun 8/314:53 pmBDL - ORD
Nonstop2h 41mUnited Airlines
Deal found 8/1$176
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/196:00 amMKE - BOS
1 stop5h 25mAmerican Airlines
Tue 8/267:00 amBOS - MKE
1 stop6h 36mAmerican Airlines
Deal found 7/31$177
This American Airlines deal was found by Cheapflights users on 8/1. 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 9/136:40 pmORD - BDL
Nonstop2h 16mAmerican Airlines
Sun 9/146:43 amBDL - ORD
Nonstop2h 37mAmerican Airlines
Deal found 8/1$177

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 August 2, 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

Fri 9/12

3:48 pm-7:19 pm

Nonstop2h 31m

Boston Logan Intl

Sun 9/14

6:10 am-8:05 am

Nonstop2h 55m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 9/14

6:05 am-9:32 am

Nonstop2h 27m

Boston Logan Intl

Sun 9/21

5:00 am-6:51 am

Nonstop2h 51m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/11

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

Mon 9/15

4:40 pm-6:55 pm

Nonstop3h 15m

$141

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/19

8:12 pm-11:18 am

1 stop14h 06m

Boston Logan Intl

Tue 8/26

6:05 am-7:07 pm

1 stop14h 02m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

10:15 am-1:48 pm

Nonstop2h 33m

Boston Logan Intl

Wed 9/10

7:55 pm-9:56 pm

Nonstop3h 01m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/12

2:55 pm-10:35 pm

1 stop6h 40m

Boston Logan Intl

Mon 9/15

10:45 am-4:25 pm

1 stop6h 40m

$157

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 8/30

5:38 pm-8:50 pm

Nonstop2h 12m

Boston Logan Intl

Tue 9/2

1:40 pm-3:08 pm

Nonstop2h 28m

$157

MinneapolisHartford

MSP - BDL

MSPBDL

Minneapolis St Paul

Fri 8/29

7:12 am-10:52 am

Nonstop2h 40m

Hartford Bradley Intl

Mon 9/1

5:28 pm-7:34 pm

Nonstop3h 06m

$165

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/20

8:12 pm-11:18 am

1 stop14h 06m

Boston Logan Intl

Sun 8/24

9:20 am-6:41 pm

1 stop10h 21m

$171

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sun 8/31

8:48 am-12:20 pm

Nonstop2h 32m

Hartford Bradley Intl

Sun 8/31

4:53 pm-6:34 pm

Nonstop2h 41m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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, 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 August 2, 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.

Weekly flight availability from Wisconsin to Massachusetts

Explore weekly flight availability from Wisconsin to Massachusetts. 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 August 2, 2025.

The most flights from USWI to USMA are scheduled on a Friday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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 August 2, 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
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,983 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,904 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,915 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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?

    $69 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Sun Country Air and JetBlue, with prices starting from $69 and $71, 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

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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 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 August 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$134Average$283FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$164Average$285FlexibilityNo cancel feeOn-time65%
DeltaCheapest$166Average$433FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$419FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$425FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$186Average$307FlexibilityNo cancel feeOn-time63%

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