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$84+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jun 9 — Jun 161
Tue 6/9
Tue 6/16
1 adult, Economy
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Cheap 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 May 10, 2026.

This Jetabroad deal was found by Cheapflights users on 5/5. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/2410:56 am
ORD
-
BOS
Nonstop2h 28m
JetBlue
Tue 6/308:10 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 5/5$166
This Delta deal was found by Cheapflights users on 5/6. 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.
Sat 5/307:00 am
ORD
-
BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Deal found 5/6$167
This Delta deal was found by Cheapflights users on 5/5. 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.
Sat 5/307:00 am
ORD
-
BOS
Nonstop2h 35m
Delta
Sun 5/317:35 am
BOS
-
ORD
Nonstop2h 52m
Delta
Deal found 5/5$172
This Flysmarter deal was found by Cheapflights users on 5/6. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:56 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Sun 5/316:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/6$174
This United Airlines deal was found by Cheapflights users on 5/8. 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.
Sat 5/307:45 pm
ORD
-
BOS
Nonstop2h 36m
United Airlines
Tue 6/25:05 pm
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 5/8$177
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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.
Fri 5/298:40 am
MSP
-
BDL
Nonstop2h 32m
Sun Country Air
Mon 6/111:12 am
BDL
-
MSP
Nonstop2h 58m
Sun Country Air
Deal found 5/5$178
This Cheapflightsfares deal was found by Cheapflights users on 5/6. 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.
Wed 5/278:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Sat 6/611:00 am
BOS
-
ORD
Nonstop2h 59m
JetBlue
Deal found 5/6$181
This Cheapflightsfares deal was found by Cheapflights users on 5/6. 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.
Thu 5/288:50 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Mon 6/16:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/6$182
This Cheapflightsfares deal was found by Cheapflights users on 5/5. 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.
Wed 5/204:58 pm
MKE
-
BOS
Nonstop2h 15m
JetBlue
Fri 5/226:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/5$182
This United Airlines deal was found by Cheapflights users on 5/5. 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 6/1712:53 pm
ORD
-
BOS
Nonstop2h 36m
United Airlines
Sun 6/217:19 am
BOS
-
ORD
Nonstop2h 57m
United Airlines
Deal found 5/5$186
This United Airlines deal was found by Cheapflights users on 5/8. 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.
Sat 5/237:45 pm
ORD
-
BOS
Nonstop2h 36m
United Airlines
Sat 5/305:45 am
BOS
-
ORD
1 stop4h 51m
United Airlines
Deal found 5/8$187
This American Airlines deal was found by Cheapflights users on 5/9. 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 7/96:17 pm
MKE
-
BOS
1 stop5h 20m
American Airlines
Tue 7/147:27 pm
BOS
-
MKE
1 stop5h 25m
American Airlines
Deal found 5/9$187

Find flight deals from Wisconsin to Massachusetts

Keep the following information in mind while searching for Wisconsin to Massachusetts flight deals. Data was last updated May 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$167
(Delta)

One-way from

$84
(United Airlines)

Popular in

February

Cheapest in

September

Average price

$279

Good round-trip deal

$198 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
Search Deals
From Wisconsin to Massachusetts
Search Deals
One-way flight from Wisconsin to Massachusetts
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($62 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 May 2026
Search Deals
Price to beat on a round-trip flight from Wisconsin to Massachusetts.
Search Deals
Price to beat on a one-way flight from Wisconsin to Massachusetts.
Search Deals

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 May 10, 2026.
Use the filters below to find and compare flights from Wisconsin to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/30

1:56 pm-5:27 pm

Nonstop2h 31m

Boston Logan Intl

Sun 5/31

6:00 am-8:00 am

Nonstop3h 00m

$182
Quickest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/21

10:28 am-1:59 pm

Nonstop2h 31m

Boston Logan Intl

Fri 7/24

8:45 pm-10:39 pm

Nonstop2h 54m

$201

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 7/1

7:23 pm-1:14 am

1 stop4h 51m

Boston Logan Intl

Tue 7/7

6:00 am-9:53 am

1 stop4h 53m

$205

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/16

7:10 am-10:46 am

Nonstop2h 36m

Boston Logan Intl

Wed 6/17

7:30 am-9:28 am

Nonstop2h 58m

$205

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/20

2:40 pm-10:30 pm

1 stop6h 50m

Boston Logan Intl

Mon 5/25

8:25 am-12:50 pm

1 stop5h 25m

$212

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/30

6:00 am-11:16 am

1 stop4h 16m

Boston Logan Intl

Wed 7/8

6:43 pm-8:40 pm

Nonstop2h 57m

$221

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/22

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

Tue 5/26

9:40 am-11:33 am

Nonstop2h 53m

$222

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/28

2:40 pm-11:55 pm

2 stops8h 15m

Boston Logan Intl

Mon 6/1

5:30 am-12:50 pm

2 stops8h 20m

$227

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 7/18

4:59 pm-11:59 pm

1 stop6h 00m

Boston Logan Intl

Sat 7/25

11:40 am-1:15 pm

Nonstop2h 35m

$237

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 7/5

8:20 pm-11:51 pm

Nonstop2h 31m

Boston Logan Intl

Fri 7/10

5:20 pm-7:25 pm

Nonstop3h 05m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/8

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Wisconsin to Massachusetts?

The best time to book flights from Wisconsin to Massachusetts is 62 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, September is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $78). Flying from Wisconsin to Massachusetts in March is currently the most expensive (average of $197). 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 May 10, 2026.

A simple way to save on the total cost of your ticket is to fly from Wisconsin to Massachusetts in the evening. If you’re flexible enough to do this you can expect to save up to 77% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Wisconsin to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Massachusetts. Price data was last updated on May 9, 2026.

Travelers seeking maximum savings on their Wisconsin to Massachusetts flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Tuesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 May 10, 2026.

The most flights from USWI to USMA are scheduled on a Tuesday (9 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from Wisconsin to Massachusetts?

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 May 10, 2026.
Read through reviews of airlines operating flights from Wisconsin to Massachusetts, such as Southwest,Delta, andUnited 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
4,304 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,304 reviews
Southwest
8.0
Very good
4,304 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,454 reviews
Southwest
8.0
Very good
4,304 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,694 reviews
Southwest
8.0
Very good
4,304 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,977 reviews
Southwest
8.0
Very good
4,304 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,667 reviews
Southwest
8.0
Very good
4,304 reviews

Crew

8.6

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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, 7 users have taken a look at flights from Wisconsin to Massachusetts.

  • How long is the flight from Wisconsin to Massachusetts?

    For as low as $182, JetBlue can have you in Massachusetts from Wisconsin in 2h 31m. 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?

    $78 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 American Airlines, with prices starting from $88 and $98, 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, September is the cheapest month in which you can book a flight from Wisconsin to Massachusetts (average of $78). Flying from Wisconsin to Massachusetts in March is currently the most expensive (average of $197). 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 5 airlines flying from Wisconsin to Massachusetts

Discover the top 5 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 May 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$88Average$241FlexibilityNo cancel feeOn-time62%
DeltaCheapest$103Average$364FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$258FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$381FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$192Average$387FlexibilityNo cancel feeOn-time69%

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