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Wisconsin

$88+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Jun 18 — Jun 251
Thu 6/18
Thu 6/25
1 adult, Economy
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Cheap 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 May 19, 2026.

This SmartFares deal was found by Cheapflights users on 5/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Tue 6/98:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 5/15$173
This SmartFares deal was found by Cheapflights users on 5/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Mon 6/88:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 5/17$176
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Wed 6/108:50 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Deal found 5/19$182
This flygcity.se deal was found by Cheapflights users on 5/17. 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 flygcity.se is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/611:00 am
BOS
-
ORD
Nonstop2h 59m
JetBlue
Mon 6/88:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 5/17$183
This SmartFares deal was found by Cheapflights users on 5/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:20 pm
BOS
-
ORD
Nonstop3h 05m
JetBlue
Tue 8/2510:56 am
ORD
-
BOS
Nonstop2h 27m
JetBlue
Deal found 5/17$184
This American Airlines deal was found by Cheapflights users on 5/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/23:00 pm
BOS
-
ORD
Nonstop3h 06m
American Airlines
Tue 6/91:57 pm
ORD
-
BOS
Nonstop2h 35m
American Airlines
Deal found 5/16$186
This United Airlines deal was found by Cheapflights users on 5/19. 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.
Wed 6/38:15 am
BOS
-
MKE
1 stop5h 40m
United Airlines
Sat 6/63:12 pm
MKE
-
BOS
1 stop5h 44m
United Airlines
Deal found 5/19$187
This Delta deal was found by Cheapflights users on 5/18. 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.
Wed 6/37:35 am
BOS
-
ORD
Nonstop2h 52m
Delta
Wed 6/107:10 am
ORD
-
BOS
Nonstop2h 36m
Delta
Deal found 5/18$187
This Frontier deal was found by Cheapflights users on 5/18. 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 8/259:12 am
BOS
-
ORD
1 stop11h 43m
Frontier
Tue 9/11:50 pm
ORD
-
BOS
1 stop10h 37m
Frontier
Deal found 5/18$189
This Expedia deal was found by Cheapflights users on 5/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
BOS
-
MKE
1 stop6h 13m
Frontier
Wed 6/2412:08 pm
MKE
-
BOS
1 stop12h 19m
Frontier
Deal found 5/18$190
This Expedia deal was found by Cheapflights users on 5/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:10 am
BOS
-
ORD
1 stop11h 40m
Frontier
Wed 6/171:29 pm
ORD
-
BOS
1 stop10h 58m
Frontier
Deal found 5/18$190
This Cheapflightsfares deal was found by Cheapflights users on 5/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Thu 6/48:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 5/19$191

Find flight deals from Massachusetts to Wisconsin

Keep the following information in mind while searching for Massachusetts to Wisconsin flight deals. Data was last updated May 19, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$173
(SmartFares)

One-way from

$88
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$279

Good round-trip deal

$173 or less

Good one-way deal

$123 or less
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Milwaukee-Mitchell flights.
Search Deals
From Massachusetts to Wisconsin
Search Deals
One-way flight from Massachusetts to Wisconsin
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 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 Massachusetts to Wisconsin.
Search Deals
Price to beat on a one-way flight from Massachusetts to Wisconsin.
Search Deals

Cheapflights Fare Finder

 
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 2,558,603 searches. Data last updated May 19, 2026.
Use the filters below to find and compare flights from Massachusetts to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/10

8:37 am-10:40 am

Nonstop3h 03m

Chicago O'Hare Intl

Thu 6/11

6:04 am-9:30 am

Nonstop2h 26m

$196

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 6/1

8:15 am-10:12 am

Nonstop2h 57m

Chicago O'Hare Intl

Tue 6/16

3:55 pm-7:30 pm

Nonstop2h 35m

$197

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/17

6:43 pm-8:40 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sun 7/19

9:41 pm-1:14 am

Nonstop2h 33m

$205

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 6/12

8:20 pm-10:20 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 6/15

9:41 pm-1:14 am

Nonstop2h 33m

$205
Quickest round-trip

BostonMilwaukee

BOS - MKE

BOSMKE

Boston Logan Intl

Wed 6/3

6:15 am-7:51 am

Nonstop2h 36m

Milwaukee-Mitchell

Sat 6/6

8:41 am-11:59 am

Nonstop2h 18m

$207

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 6/24

8:45 pm-10:42 pm

Nonstop2h 57m

Chicago O'Hare Intl

Tue 6/30

7:10 am-10:46 am

Nonstop2h 36m

$207

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 6/15

7:30 am-9:28 am

Nonstop2h 58m

Chicago O'Hare Intl

Sat 6/20

7:10 am-10:46 am

Nonstop2h 36m

$207

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/27

7:35 am-4:05 pm

2 stops9h 30m

Chicago O'Hare Intl

Fri 5/29

2:40 pm-11:55 pm

2 stops8h 15m

$231

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 5/25

7:35 am-9:27 am

Nonstop2h 52m

Chicago O'Hare Intl

Fri 5/29

10:25 am-1:49 pm

Nonstop2h 24m

$231

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 5/24

9:50 am-11:43 am

Nonstop2h 53m

Chicago O'Hare Intl

Tue 5/26

9:41 pm-1:14 am

Nonstop2h 33m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Showing 1-10 of 60 resultsSorted by cheapest first
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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.

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Wisconsin

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

Currently, April is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $68). Flying from Massachusetts to Wisconsin in March is currently the most expensive (average of $207). 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 May 19, 2026.

When flying from Massachusetts to Wisconsin, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 17% versus a flight in the morning.

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

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

Booking 66 days in advance of your planned departure date is, on average, the best time to get cheap flights from Massachusetts to Wisconsin. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Wisconsin. Price data was last updated on May 16, 2026.

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

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 May 19, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Massachusetts to Wisconsin by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,284 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
7.9
Good
4,284 reviews
Southwest
7.9
Good
4,284 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
8,452 reviews
Southwest
7.9
Good
4,284 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
9,732 reviews
Southwest
7.9
Good
4,284 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
2,982 reviews
Southwest
7.9
Good
4,284 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

Comfort

8.0

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
11,645 reviews
Southwest
7.9
Good
4,284 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Crew

8.6

Entertainment

7.5

Comfort

8.0

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 Massachusetts to Wisconsin. 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 Massachusetts to Wisconsin flight route?

    Within the past month, 1 users have taken a look at flights from Massachusetts to Wisconsin.

  • How long is the flight from Massachusetts to Wisconsin?

    A quick flight from Massachusetts to Wisconsin can take about 2h 36m. American Airlines provides one of the quickest options available for as low as $207. Airlines will cover a distance of 857 mi. Generally, flights for this route are nonstop.

  • 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 American Airlines ($88), JetBlue ($88), and Southwest ($98).

  • 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, April is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $68). Flying from Massachusetts to Wisconsin in March is currently the most expensive (average of $207). 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 Massachusetts to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Massachusetts to Wisconsin

Discover the top 5 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 2,558,603 searches. Data last updated May 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$98Average$264FlexibilityNo cancel feeOn-time62%
DeltaCheapest$137Average$401FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$272FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$176Average$468FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$206Average$444FlexibilityNo cancel feeOn-time71%

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