$69+ Cheap flights from Boston (BOS) 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
Jan 30 — Feb 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 Boston to Wisconsin
Cheapest flights from Boston to WisconsinExplore the most affordable flight options available from Boston to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 31, 2025.
Explore the most affordable flight options available from Boston to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 31, 2025.
This American Airlines deal was found by Cheapflights users on 12/28. 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.
Wed 12/315:40 pmBOS - ORD
Nonstop3h 12mAmerican Airlines
Thu 1/18:20 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 12/28![American Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 12/28. 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.
Wed 12/315:40 pmBOS - ORD
Nonstop3h 12mAmerican Airlines
Fri 1/24:07 pmORD - BOS
1 stop5h 09mAmerican Airlines
Deal found 12/28![American Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 12/28. 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 12/317:44 pmBOS - ORD
1 stop5h 00mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/28![United Airlines logo]()
$265
This Expedia deal was found by Cheapflights users on 12/30. 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 12/315:05 pmBOS - ORD
1 stop5h 59mJetBlue
Sun 1/47:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/30![JetBlue logo]()
$272
This United Airlines deal was found by Cheapflights users on 12/29. 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 12/306:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Thu 1/19:20 amORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/29![United Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 12/29. 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 12/307:32 pmBOS - ORD
1 stop5h 03mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/29![United Airlines logo]()
$292
This United Airlines deal was found by Cheapflights users on 12/28. 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 12/315:20 amBOS - ORD
1 stop5h 18mUnited Airlines
Mon 1/56:21 pmORD - BOS
1 stop4h 33mUnited Airlines
Deal found 12/28![United Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 12/29. 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 12/304:36 pmBOS - GRB
1 stop8h 00mAmerican Airlines
Tue 1/64:53 pmGRB - BOS
1 stop5h 51mAmerican Airlines
Deal found 12/29![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/314:15 pmBOS - MSN
1 stop5h 48mUnited Airlines
Thu 1/15:26 pmMSN - BOS
1 stop6h 19mUnited Airlines
Deal found 12/30![United Airlines logo]()
$372
This Expedia deal was found by Cheapflights users on 12/29. 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 12/3111:49 amBOS - MSP
Nonstop3h 11mMultiple Airlines
Sun 1/411:29 amMSP - BOS
1 stop12h 50mMultiple Airlines
Deal found 12/29![Multiple Airlines logo]()
$391
This Sun Country Air deal was found by Cheapflights users on 12/29. 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.
Wed 12/3111:49 amBOS - MSP
Nonstop3h 11mSun Country Air
Sat 1/36:54 amMSP - BOS
Nonstop2h 57mSun Country Air
Deal found 12/29![Sun Country Air logo]()
$398
This Orbitz deal was found by Cheapflights users on 12/29. 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.
Tue 12/3011:49 amBOS - MSP
Nonstop3h 11mMultiple Airlines
Thu 1/111:49 amMSP - BOS
1 stop12h 30mMultiple Airlines
Deal found 12/29![Multiple Airlines logo]()
$437
Find flight deals from Boston to Wisconsin
Keep the following information in mind while searching for Boston to Wisconsin flight deals. Data was last updated December 31, 2025.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $125 (Trip.com) |
One-way from | $69 (United Airlines) |
Popular in | November |
Cheapest in | September |
Average price | $396 |
Good round-trip deal | $299 or less |
Good one-way deal | $248 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Boston 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 December 31, 2025.
Use the filters below to find and compare flights from Boston to Wisconsin that are best for you.
Fly from
Boston
Fly to
Wisconsin
Route
Depart
Return
Price
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 1/30
11:30 am-1:39 pm
Nonstop3h 09m
Chicago O'Hare Intl
Thu 2/5
7:05 am-10:40 am
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 1/5
7:45 am-9:49 am
Nonstop3h 04m
Chicago O'Hare Intl
Mon 1/12
4:15 pm-7:39 pm
Nonstop2h 24m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 3/29
3:20 pm-5:24 pm
Nonstop3h 04m
Chicago O'Hare Intl
Fri 4/3
10:00 am-1:27 pm
Nonstop2h 27m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/22
4:10 pm-6:19 pm
Nonstop3h 09m
Chicago O'Hare Intl
Sun 1/25
7:05 am-10:40 am
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 2/1
7:30 am-9:41 am
Nonstop3h 11m
Chicago O'Hare Intl
Mon 2/2
10:40 am-2:13 pm
Nonstop2h 33m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 1/26
5:23 pm-8:18 am
1 stop15h 55m
Chicago O'Hare Intl
Wed 1/28
10:48 am-11:19 pm
1 stop11h 31m
$141
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 1/17
4:49 pm-6:49 pm
Nonstop3h 00m
Chicago O'Hare Intl
Mon 1/19
7:30 am-10:52 am
Nonstop2h 22m
$141
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 2/25
7:00 am-9:10 am
Nonstop3h 10m
Chicago O'Hare Intl
Fri 2/27
6:04 am-2:16 pm
1 stop7h 12m
$142
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 1/27
3:35 pm-5:43 pm
Nonstop3h 08m
Chicago O'Hare Intl
Tue 2/3
9:40 am-6:48 pm
1 stop8h 08m
$142
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/22
12:15 pm-7:36 pm
1 stop8h 21m
Chicago O'Hare Intl
Sun 1/25
7:45 am-11:10 am
Nonstop2h 25m
$142
Showing 1-10 of 60 results
Best time to book a flight from Boston to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Boston 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 Boston to Wisconsin
What is the cheapest month to book a flight from Boston to Wisconsin?
Currently, September is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $98). Flying from Boston to Wisconsin in December is currently the most expensive (average of $258). 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 BOS to WI?
Find hourly flight availability from Boston 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 December 31, 2025.
It’s optimal to fly from Boston to Wisconsin in the morning. By choosing this option you can save up to 46% on the cost of your flight, compared to a flight in the evening.
What is the cheapest day to fly from Boston to Wisconsin?
Use this chart to determine the cheapest time to fly round-trip from Boston to Wisconsin. Price data was last updated on December 27, 2025.
Travelers seeking maximum savings on their Boston 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.
Weekly flight availability from Boston to Wisconsin
Explore weekly flight availability from Boston to Wisconsin. 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 December 31, 2025.
The most flights from BOS to USWI are scheduled on a Tuesday (3 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (1 on average).
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 December 31, 2025.
Read through reviews of airlines operating flights from Boston to Wisconsin, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
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 Boston to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Boston to Wisconsin
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Boston to Wisconsin
Discover the top 5 airlines that operate flights from Boston 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 December 31, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$296 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$279 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$183 | Average$455 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$433 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$434 | FlexibilityNo cancel fee | On-time69% |