$57+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Feb 27 — Mar 61
1 adult, Economy
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Massachusetts to Wisconsin
Cheapest flights from Massachusetts to WisconsinExplore 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 January 28, 2026.
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 January 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Sun 3/16:00 am
BOS
- ORD
1 stop29h 51m
Frontier
Wed 3/411:51 am
ORD
- BOS
1 stop12h 22m
Frontier
Deal found 1/25![Frontier logo]()
$132
This Super.com deal was found by Cheapflights users on 1/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/53:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Thu 2/1210:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 1/26![JetBlue logo]()
$133
This Super.com deal was found by Cheapflights users on 1/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/112:50 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Tue 2/1710:00 am
ORD
- BOS
Nonstop2h 20m
JetBlue
Deal found 1/27![JetBlue logo]()
$134
This United Airlines deal was found by Cheapflights users on 1/26. 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 1/309:30 am
BOS
- ORD
Nonstop3h 04m
United Airlines
Wed 2/48:10 am
ORD
- BOS
Nonstop2h 23m
United Airlines
Deal found 1/26![United Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 1/3012:55 pm
BOS
- ORD
Nonstop3h 18m
American Airlines
Sun 2/17:00 am
ORD
- BOS
Nonstop2h 23m
American Airlines
Deal found 1/27![American Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 1/27. 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 2/114:10 pm
BOS
- ORD
Nonstop3h 09m
Delta
Sun 2/157:05 am
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 1/27![Delta logo]()
$137
This deal was found by Cheapflights users on 1/26. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:51 pm
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 7/197:10 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 1/26![Sun Country Air logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Fri 2/276:00 am
BOS
- ORD
1 stop29h 51m
Multiple Airlines
Mon 3/27:23 pm
ORD
- BOS
1 stop27h 36m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$138
This Trip.com deal was found by Cheapflights users on 1/25. 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.
Sun 2/13:20 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Thu 2/57:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Deal found 1/25![JetBlue logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Thu 2/266:00 am
BOS
- ORD
1 stop17h 39m
Frontier
Wed 3/411:51 am
ORD
- BOS
1 stop12h 22m
Frontier
Deal found 1/26![Frontier logo]()
$141
This Travelocity deal was found by Cheapflights users on 1/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:00 am
BOS
- ORD
Nonstop3h 10m
Multiple Airlines
Mon 3/24:42 pm
ORD
- BOS
1 stop7h 31m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$142
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Mon 2/96:21 pm
BOS
- ORD
Nonstop3h 04m
United Airlines
Fri 2/137:30 am
ORD
- BOS
Nonstop2h 19m
United Airlines
Deal found 1/26![United Airlines logo]()
$144
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 January 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $132 (Kiwi.com) |
One-way from | $57 (Kiwi.com) |
Popular in | November |
Cheapest in | September |
Average price | $355 |
Good round-trip deal | $298 or less |
Good one-way deal | $228 or less |
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 January 28, 2026.
Use the filters below to find and compare flights from Massachusetts to Wisconsin that are best for you.
Fly from
Massachusetts
Fly to
Wisconsin
Route
Depart
Return
Price
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/11
4:25 pm-6:31 pm
Nonstop3h 06m
Chicago O'Hare Intl
Tue 3/24
7:35 pm-11:02 pm
Nonstop2h 27m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 2/24
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Wed 2/25
10:00 am-1:20 pm
Nonstop2h 20m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 7/8
12:20 pm-2:07 pm
Nonstop2h 47m
Chicago O'Hare Intl
Mon 7/13
6:00 am-9:24 am
Nonstop2h 24m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/2
8:55 am-11:00 am
Nonstop3h 05m
Chicago O'Hare Intl
Sat 5/9
7:00 am-10:28 am
Nonstop2h 28m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 3/4
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Wed 3/4
12:59 pm-7:58 pm
1 stop5h 59m
$146
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/3
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Fri 3/6
6:04 am-2:09 pm
1 stop7h 05m
$151
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 3/1
7:07 am-12:04 pm
1 stop5h 57m
Chicago O'Hare Intl
Tue 3/3
10:00 am-1:20 pm
Nonstop2h 20m
$151
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 3/2
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Tue 3/3
6:04 am-2:09 pm
1 stop7h 05m
$151
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 2/28
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Mon 3/2
12:41 pm-7:58 pm
1 stop6h 17m
$151
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 3/1
7:15 am-9:28 am
Nonstop3h 13m
Chicago O'Hare Intl
Mon 3/2
7:05 am-10:37 am
Nonstop2h 32m
$156
Showing 1-10 of 60 results
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, September is the cheapest month in which you can book a flight from Massachusetts to Wisconsin (average of $98). Flying from Massachusetts to Wisconsin in December is currently the most expensive (average of $254). 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 January 28, 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 50% versus a flight in the evening.
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 January 24, 2026.
Travelers seeking maximum savings on their Massachusetts to Wisconsin flight should consider departing on Tuesday at noon when fares are most often at their lowest. Monday mornings 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 January 28, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United 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.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Overall
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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.
Browse thousands of different options on Cheapflights for your next trip
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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.
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 January 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$98 | Average$282 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$436 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$137 | Average$433 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$271 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$196 | Average$425 | FlexibilityNo cancel fee | On-time71% |