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Massachusetts

$69+ 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 9/23. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$127
(JetBlue)

One-way from

$69
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$277

Good round-trip deal

$180 or less

Good one-way deal

$266 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. 15% potential increase in price ($57 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

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.
Mon 9/297:50 pmORD - BOS
Nonstop2h 35mJetBlue
Sat 10/47:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/15$127
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.
Wed 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
Wed 10/14:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 9/15$130
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.
Fri 9/267:50 pmORD - BOS
Nonstop2h 35mJetBlue
Wed 10/17:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/14$132
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/11:30 pmORD - BOS
Nonstop2h 32mUnited Airlines
Sun 10/56:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 9/14$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.
Thu 11/611:20 amORD - BOS
Nonstop2h 24mJetBlue
Wed 11/123:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 9/15$135
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.
Wed 10/86:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Wed 10/156:16 amBOS - ORD
1 stop18h 29mSpirit Airlines
Deal found 9/15$136
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.
Tue 9/2311:05 amORD - BOS
Nonstop2h 35mUnited Airlines
Wed 9/244:27 pmBOS - ORD
Nonstop2h 54mUnited Airlines
Deal found 9/16$137
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.
Thu 10/309:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
Sat 11/16:26 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 9/16$138
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.
Tue 10/286:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Wed 10/296:16 amBOS - ORD
1 stop13h 22mSpirit Airlines
Deal found 9/14$139
This Orbitz 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:50 pmORD - BOS
1 stop12h 53mMultiple Airlines
Tue 10/73:00 pmBOS - ORD
1 stop9h 45mMultiple Airlines
Deal found 9/14$140
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.
Sat 10/1811:55 amORD - BOS
1 stop11h 04mSpirit Airlines
Tue 10/213:00 pmBOS - ORD
1 stop9h 45mSpirit Airlines
Deal found 9/14$141
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/267:50 pmORD - BOS
Nonstop2h 35mJetBlue
Sat 9/277:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/14$142

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 September 16, 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

Wed 1/7

7:00 am-10:33 am

Nonstop2h 33m

Boston Logan Intl

Sun 1/11

7:00 am-9:10 am

Nonstop3h 10m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/13

11:25 am-2:49 pm

Nonstop2h 24m

Boston Logan Intl

Wed 12/17

8:30 am-10:35 am

Nonstop3h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 11/26

1:06 pm-4:34 pm

Nonstop2h 28m

Boston Logan Intl

Sat 11/29

5:35 pm-7:50 pm

Nonstop3h 15m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/14

1:45 pm-11:15 pm

1 stop8h 30m

Boston Logan Intl

Wed 11/19

9:05 am-9:50 pm

2 stops13h 45m

$148

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/18

10:08 am-1:37 pm

Nonstop2h 29m

Boston Logan Intl

Fri 10/24

4:05 pm-6:18 pm

Nonstop3h 13m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/6

9:25 pm-12:45 am

Nonstop2h 20m

Boston Logan Intl

Sat 11/15

6:00 am-10:45 am

1 stop5h 45m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 10/20

7:30 am-11:02 am

Nonstop2h 32m

Boston Logan Intl

Wed 10/22

5:30 am-9:36 am

1 stop5h 06m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/14

6:21 pm-9:49 pm

Nonstop2h 28m

Boston Logan Intl

Mon 11/17

7:38 pm-11:43 pm

1 stop5h 05m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 1/5

7:00 am-10:33 am

Nonstop2h 33m

Boston Logan Intl

Thu 1/15

8:10 pm-10:15 pm

Nonstop3h 05m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/6

9:50 am-1:16 pm

Nonstop2h 26m

Boston Logan Intl

Mon 1/12

6:40 pm-8:59 pm

Nonstop3h 19m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 September 16, 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 September 16, 2025.

The most flights from USWI to USMA are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 September 16, 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
4,242 reviews

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

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

  • How popular is this Wisconsin to Massachusetts flight route?

    Within the past month, 6 users have taken a look at flights from Wisconsin to Massachusetts.

  • How long is the flight from Wisconsin to Massachusetts?

    For as low as $137, Delta can have you in Massachusetts from Wisconsin in 2h 24m. Airlines will cover a distance of 864 mi. This flight may include one or multiple stops.

  • 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 JetBlue. You may also be able to find cheap deals on Southwest and United Airlines, with prices starting from $69 and $89, 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$119Average$280FlexibilityNo cancel feeOn-time62%
DeltaCheapest$160Average$433FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$164Average$267FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$184Average$429FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$186Average$289FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$413FlexibilityNo cancel feeOn-time69%

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