$68+ 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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Feb 20 — Feb 271
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 21, 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 21, 2026.
This JetBlue deal was found by Cheapflights users on 1/19. 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.
Wed 2/112:50 pm
BOS
- ORD
Nonstop3h 05m
JetBlue
Sun 2/156:04 am
ORD
- BOS
1 stop7h 20m
JetBlue
Deal found 1/19![JetBlue logo]()
$132
This Expedia deal was found by Cheapflights users on 1/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/63:35 pm
BOS
- ORD
Nonstop3h 08m
Multiple Airlines
Tue 2/106:07 pm
ORD
- BOS
1 stop6h 06m
Multiple Airlines
Deal found 1/20![Multiple Airlines logo]()
$133
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 2/285:54 pm
BOS
- ORD
Nonstop3h 06m
American Airlines
Sun 3/16:26 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Deal found 1/20![American Airlines logo]()
$134
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/296:00 am
BOS
- ORD
Nonstop3h 04m
United Airlines
Thu 1/294:15 pm
ORD
- BOS
Nonstop2h 24m
United Airlines
Deal found 1/20![United Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 1/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:52 am
BOS
- ORD
Nonstop3h 11m
American Airlines
Thu 3/126:26 am
ORD
- BOS
Nonstop2h 28m
American Airlines
Deal found 1/18![American Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/75:15 pm
BOS
- ORD
Nonstop3h 11m
Delta
Sun 2/87:05 am
ORD
- BOS
Nonstop2h 35m
Delta
Deal found 1/20![Delta logo]()
$137
This Sun Country Air deal was found by Cheapflights users on 1/19. 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.
Sun 7/1211:58 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Sun 7/197:10 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 1/19![Sun Country Air logo]()
$138
This Rumbo deal was found by Cheapflights users on 1/19. 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 Rumbo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/710:15 am
BOS
- ORD
1 stop10h 16m
JetBlue
Sun 2/87:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Deal found 1/19![JetBlue logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 2/175:50 pm
BOS
- ORD
1 stop16h 49m
Multiple Airlines
Wed 2/2511:51 am
ORD
- BOS
1 stop12h 22m
Multiple Airlines
Deal found 1/19![Multiple Airlines logo]()
$141
This United Airlines deal was found by Cheapflights users on 1/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:45 am
BOS
- ORD
Nonstop3h 05m
United Airlines
Sun 3/17:10 am
ORD
- BOS
1 stop4h 43m
United Airlines
Deal found 1/20![United Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Wed 2/185:50 pm
BOS
- ORD
1 stop16h 49m
Multiple Airlines
Wed 2/2511:51 am
ORD
- BOS
1 stop12h 22m
Multiple Airlines
Deal found 1/19![Multiple Airlines logo]()
$143
This Booking.com deal was found by Cheapflights users on 1/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/511:52 am
BDL
- MSP
Nonstop2h 59m
Sun Country Air
Mon 6/87:20 am
MSP
- BDL
Nonstop2h 37m
Sun Country Air
Deal found 1/19![Sun Country Air logo]()
$148
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 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | Expedia 3 stars |
Round-trip from | $132 (JetBlue) |
One-way from | $68 (United Airlines) |
Popular in | November |
Cheapest in | September |
Average price | $369 |
Good round-trip deal | $224 or less |
Good one-way deal | $199 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 21, 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
Sat 5/16
7:35 pm-9:36 pm
Nonstop3h 01m
Chicago O'Hare Intl
Tue 5/19
6:00 am-9:15 am
Nonstop2h 15m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 2/6
8:25 pm-10:29 pm
Nonstop3h 04m
Chicago O'Hare Intl
Sun 2/8
7:05 am-10:40 am
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/26
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Mon 3/2
12:41 pm-7:58 pm
1 stop6h 17m
$140
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/5
9:30 am-2:25 pm
1 stop5h 55m
Chicago O'Hare Intl
Sun 2/8
7:30 am-10:52 am
Nonstop2h 22m
$152
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 2/11
2:50 pm-4:55 pm
Nonstop3h 05m
Chicago O'Hare Intl
Thu 2/12
6:04 am-2:24 pm
1 stop7h 20m
$152
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 3/5
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Fri 3/6
6:04 am-2:35 pm
1 stop7h 31m
$152
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/16
7:00 am-8:58 am
Nonstop2h 58m
Chicago O'Hare Intl
Tue 5/19
7:00 am-10:28 am
Nonstop2h 28m
$156
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/19
7:15 am-9:28 am
Nonstop3h 13m
Chicago O'Hare Intl
Fri 2/27
7:05 am-10:37 am
Nonstop2h 32m
$157
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/10
4:25 pm-6:31 pm
Nonstop3h 06m
Chicago O'Hare Intl
Wed 3/18
10:40 am-2:04 pm
Nonstop2h 24m
$161
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 6/13
8:10 pm-10:06 pm
Nonstop2h 56m
Chicago O'Hare Intl
Tue 6/23
7:00 am-10:28 am
Nonstop2h 28m
$161
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 21, 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 52% 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 17, 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.
How much does it cost to fly round-trip from Massachusetts to Wisconsin?
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 21, 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.
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Overall
8.0
Comfort
8.0
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Overall
8.0
Comfort
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 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$99 | Average$283 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$433 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$140 | Average$443 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$270 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$196 | Average$433 | FlexibilityNo cancel fee | On-time71% |