$68+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Feb 10 — Feb 171
1 adult, Economy
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Find cheap flights from Boston to Wisconsin with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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
Keep the following information in mind while searching for Boston to Wisconsin flight deals. Data was last updated January 11, 2026.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $128 (Priceline) |
One-way from | $68 (Southwest) |
Popular in | November |
Cheapest in | September |
Average price | $355 |
Good round-trip deal | $224 or less |
Good one-way deal | $198 or less |
Find 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 January 11, 2026.
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 January 11, 2026.
This Priceline deal was found by Cheapflights users on 1/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/36:00 amBOS - ORD
1 stop8h 58mFrontier
Wed 2/116:02 pmORD - BOS
1 stop6h 11mFrontier
Deal found 1/10![Frontier logo]()
$128
This Frontier deal was found by Cheapflights users on 1/10. 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 2/246:00 amBOS - ORD
1 stop11h 52mFrontier
Tue 3/36:02 pmORD - BOS
1 stop6h 11mFrontier
Deal found 1/10![Frontier logo]()
$129
This lastminute.com deal was found by Cheapflights users on 1/9. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/223:35 pmBOS - ORD
Nonstop3h 08mJetBlue
Mon 1/267:40 amORD - BOS
Nonstop2h 25mJetBlue
Deal found 1/9![JetBlue logo]()
$130
This Southwest deal was found by Cheapflights users on 1/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:00 amBOS - ORD
1 stop8h 15mSouthwest
Mon 2/91:45 pmORD - BOS
1 stop8h 10mSouthwest
Deal found 1/8![Southwest logo]()
$131
This Priceline deal was found by Cheapflights users on 1/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/36:00 amBOS - ORD
1 stop8h 58mMultiple Airlines
Wed 3/1810:56 amORD - BOS
Nonstop2h 24mMultiple Airlines
Deal found 1/11![Multiple Airlines logo]()
$133
This United Airlines deal was found by Cheapflights users on 1/10. 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 1/234:16 pmBOS - ORD
Nonstop3h 00mUnited Airlines
Sun 1/257:30 amORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 1/10![United Airlines logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 1/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/302:00 pmBOS - ORD
1 stop8h 03mSpirit Airlines
Tue 2/310:48 amORD - BOS
1 stop11h 31mSpirit Airlines
Deal found 1/8![Spirit Airlines logo]()
$136
This United Airlines deal was found by Cheapflights users on 1/8. 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 5/27:15 amBOS - ORD
Nonstop2h 44mUnited Airlines
Sat 5/97:10 amORD - BOS
Nonstop2h 23mUnited Airlines
Deal found 1/8![United Airlines logo]()
$137
This JetBlue deal was found by Cheapflights users on 1/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/177:00 amBOS - ORD
Nonstop3h 10mJetBlue
Wed 2/2510:00 amORD - BOS
Nonstop2h 20mJetBlue
Deal found 1/8![JetBlue logo]()
$138
This Frontier deal was found by Cheapflights users on 1/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/106:00 amBOS - ORD
1 stop12h 12mFrontier
Mon 2/234:42 pmORD - BOS
1 stop7h 31mFrontier
Deal found 1/8![Frontier logo]()
$139
This Expedia deal was found by Cheapflights users on 1/11. 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 2/106:00 amBOS - ORD
1 stop12h 12mMultiple Airlines
Tue 2/1710:00 amORD - BOS
Nonstop2h 20mMultiple Airlines
Deal found 1/11![Multiple Airlines logo]()
$140
This Delta deal was found by Cheapflights users on 1/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:15 pmBOS - ORD
Nonstop3h 08mDelta
Mon 2/236:00 amORD - BOS
1 stop6h 19mDelta
Deal found 1/8![Delta logo]()
$141
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 January 11, 2026.
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
Sat 2/21
5:15 pm-7:23 pm
Nonstop3h 08m
Chicago O'Hare Intl
Wed 2/25
5:37 pm-11:26 pm
1 stop4h 49m
$131
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/5
5:00 am-12:15 pm
1 stop8h 15m
Chicago O'Hare Intl
Mon 2/9
1:45 pm-10:55 pm
1 stop8h 10m
$131
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 2/2
4:16 pm-6:16 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 2/4
1:55 pm-5:19 pm
Nonstop2h 24m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/15
9:30 am-11:34 am
Nonstop3h 04m
Chicago O'Hare Intl
Sat 1/17
6:05 pm-9:38 pm
Nonstop2h 33m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 2/18
12:50 pm-4:41 pm
1 stop4h 51m
Chicago O'Hare Intl
Mon 2/23
7:10 am-1:19 pm
1 stop5h 09m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Mon 3/23
4:30 pm-6:35 pm
Nonstop3h 05m
Chicago O'Hare Intl
Wed 3/25
11:05 am-2:29 pm
Nonstop2h 24m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/5
6:00 am-8:04 am
Nonstop3h 04m
Chicago O'Hare Intl
Mon 2/9
7:30 am-10:52 am
Nonstop2h 22m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/5
6:00 am-8:04 am
Nonstop3h 04m
Chicago O'Hare Intl
Sat 2/7
2:00 pm-5:24 pm
Nonstop2h 24m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/22
7:30 am-9:41 am
Nonstop3h 11m
Chicago O'Hare Intl
Sun 1/25
7:05 am-10:40 am
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 1/28
11:30 am-1:39 pm
Nonstop3h 09m
Chicago O'Hare Intl
Sun 2/1
7:05 am-10:40 am
Nonstop2h 35m
$137
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 $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 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 January 11, 2026.
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 January 10, 2026.
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 January 11, 2026.
The most flights from BOS to USWI are scheduled on a Friday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 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 January 11, 2026.
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
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
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 Boston 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 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 January 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$297 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$176 | Average$277 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$182 | Average$452 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$196 | Average$436 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$202 | Average$433 | FlexibilityNo cancel fee | On-time69% |