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$75+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Wisconsin to Massachusetts

Discover tips and strategies to find the most affordable flight options for your journey from Wisconsin (USWI) to Massachusetts (USMA). 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 20, 2024.

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 November 20, 2024.

This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/109:58 amORD - BOS
1 stop13h 40mSpirit Airlines
Wed 12/115:00 amBOS - ORD
1 stop12h 06mSpirit Airlines
Deal found 11/20$101
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/910:59 amORD - BOS
1 stop12h 31mMultiple Airlines
Tue 12/105:00 amBOS - ORD
1 stop12h 06mMultiple Airlines
Deal found 11/19$108
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/910:59 amORD - BOS
1 stop12h 31mFrontier
Wed 12/116:00 amBOS - ORD
1 stop27h 24mFrontier
Deal found 11/19$114
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.
Fri 12/610:47 amMKE - BDL
1 stop22h 05mFrontier
Thu 12/1210:55 amBDL - MKE
1 stop23h 52mFrontier
Deal found 11/20$139
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Tue 12/101:55 pmORD - BOS
Nonstop2h 21mUnited Airlines
Tue 12/1710:45 amBOS - ORD
Nonstop2h 56mUnited Airlines
Deal found 11/19$157
This JetBlue deal was found by Cheapflights users on 11/19. 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.
Tue 12/1010:14 amORD - BOS
1 stop7h 31mJetBlue
Sun 12/156:00 amBOS - ORD
Nonstop3h 06mJetBlue
Deal found 11/19$166
This CheapOair deal was found by Cheapflights users on 11/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/65:21 pmMSP - BOS
1 stop6h 09mMultiple Airlines
Tue 12/106:01 pmBOS - MSP
1 stop23h 17mMultiple Airlines
Deal found 11/19$167
This Sun Country Air deal was found by Cheapflights users on 11/19. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/197:20 pmMSP - BOS
Nonstop2h 49mSun Country Air
Wed 12/2511:46 amBOS - MSP
Nonstop3h 12mSun Country Air
Deal found 11/19$168
This FlightHub deal was found by Cheapflights users on 11/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:00 amMSP - BOS
1 stop13h 35mSpirit Airlines
Tue 12/312:27 pmBOS - MSP
1 stop27h 18mSpirit Airlines
Deal found 11/19$171
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/156:30 amORD - BOS
Nonstop2h 30mDelta
Wed 12/187:25 amBOS - ORD
Nonstop3h 03mDelta
Deal found 11/19$177
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.
Thu 12/197:19 amORD - BOS
Nonstop2h 31mAmerican Airlines
Mon 1/208:45 amBOS - ORD
Nonstop3h 00mAmerican Airlines
Deal found 11/20$182
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.
Mon 12/166:07 pmORD - BDL
1 stop14h 45mFrontier
Wed 12/184:00 pmBDL - ORD
1 stop6h 45mFrontier
Deal found 11/20$188

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

9:58 am-12:38 am

1 stop13h 40m

Boston Logan Intl

Wed 12/11

5:00 am-4:06 pm

1 stop12h 06m

$101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/9

5:02 pm-12:30 am

1 stop6h 28m

Boston Logan Intl

Tue 1/14

6:00 am-1:34 pm

1 stop8h 34m

$108

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

9:58 am-12:38 am

1 stop13h 40m

Boston Logan Intl

Thu 12/12

6:00 am-9:54 am

1 stop28h 54m

$115

MilwaukeeHartford

MKE - BDL

MKEBDL

Milwaukee-Mitchell

Fri 12/6

10:47 am-9:52 am

1 stop22h 05m

Hartford Bradley Intl

Thu 12/12

10:55 am-9:47 am

1 stop23h 52m

$139

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

4:40 pm-8:02 pm

Nonstop2h 22m

Boston Logan Intl

Tue 12/17

1:59 pm-3:53 pm

Nonstop2h 54m

$157

MinneapolisBoston

MSP - BOS

MSPBOS

Minneapolis St Paul

Tue 1/7

1:30 pm-8:59 pm

1 stop6h 29m

Boston Logan Intl

Wed 1/8

2:27 pm-11:39 pm

1 stop10h 12m

$166

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/4

9:20 am-12:45 pm

Nonstop2h 25m

Boston Logan Intl

Sat 12/7

3:57 pm-8:07 pm

1 stop5h 10m

$167

MinneapolisBoston

MSP - BOS

MSPBOS

Minneapolis St Paul

Fri 12/6

5:21 pm-12:30 am

1 stop6h 09m

Boston Logan Intl

Tue 12/10

6:01 pm-4:18 pm

1 stop23h 17m

$167

MinneapolisBoston

MSP - BOS

MSPBOS

Minneapolis St Paul

Thu 12/19

7:20 pm-11:09 pm

Nonstop2h 49m

Boston Logan Intl

Wed 12/25

11:46 am-1:58 pm

Nonstop3h 12m

$168

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/15

6:30 am-10:00 am

Nonstop2h 30m

Boston Logan Intl

Wed 12/18

7:25 am-9:28 am

Nonstop3h 03m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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.

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 November 20, 2024.

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 November 20, 2024.
Get a feel of what it's like to fly with Frontier, American Airlines and Spirit Airlines 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
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

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

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

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 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?

    $75 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on JetBlue and Spirit Airlines, with prices starting from $79 and $80, 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.

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$34Average$166FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$133Average$287FlexibilityNo cancel feeOn-time62%
DeltaCheapest$152Average$419FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$176Average$440FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$176Average$459FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$211Average$379FlexibilityNo cancel feeOn-time63%
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