$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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Feb 17 — Feb 241
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 18, 2026.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $132 (Flysmarter) |
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 |
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 18, 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 18, 2026.
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/73:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Mon 2/99:40 am
ORD
- BOS
1 stop4h 54m
JetBlue
Deal found 1/18![JetBlue logo]()
$132
This United Airlines deal was found by Cheapflights users on 1/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2912:45 pm
BOS
- ORD
Nonstop3h 04m
United Airlines
Mon 2/27:30 am
ORD
- BOS
Nonstop2h 22m
United Airlines
Deal found 1/16![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.
Sat 2/74:18 pm
BOS
- ORD
Nonstop3h 22m
American Airlines
Mon 2/98:18 pm
ORD
- BOS
Nonstop2h 26m
American Airlines
Deal found 1/18![American Airlines logo]()
$136
This Delta deal was found by Cheapflights users on 1/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/317:30 am
BOS
- ORD
Nonstop3h 11m
Delta
Tue 2/1010:40 am
ORD
- BOS
Nonstop2h 33m
Delta
Deal found 1/15![Delta logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 1/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/26:00 am
BOS
- ORD
1 stop17h 39m
Frontier
Wed 3/411:51 am
ORD
- BOS
1 stop12h 22m
Frontier
Deal found 1/16![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 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 stop17h 39m
Frontier
Mon 3/24:42 pm
ORD
- BOS
1 stop7h 31m
Frontier
Deal found 1/17![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 1/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
BOS
- ORD
1 stop11h 52m
Multiple Airlines
Tue 3/37:23 pm
ORD
- BOS
1 stop20h 22m
Multiple Airlines
Deal found 1/17![Multiple Airlines logo]()
$141
This Delta deal was found by Cheapflights users on 1/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/278:25 pm
BOS
- ORD
Nonstop3h 04m
Delta
Fri 1/306:59 pm
ORD
- BOS
Nonstop2h 32m
Delta
Deal found 1/15![Delta logo]()
$142
This Frontier deal was found by Cheapflights users on 1/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/296:00 am
BOS
- ORD
1 stop8h 37m
Frontier
Wed 2/1112:36 pm
ORD
- BOS
1 stop11h 37m
Frontier
Deal found 1/15![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 1/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/103:43 pm
BOS
- MKE
1 stop25h 01m
Multiple Airlines
Mon 2/167:52 pm
MKE
- BOS
1 stop25h 09m
Multiple Airlines
Deal found 1/16![Multiple Airlines logo]()
$182
This Frontier deal was found by Cheapflights users on 1/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- MKE
1 stop12h 25m
Frontier
Mon 3/25:30 pm
MKE
- BOS
1 stop6h 43m
Frontier
Deal found 1/16![Frontier logo]()
$195
This Sun Country Air deal was found by Cheapflights users on 1/16. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:17 am
BOS
- MSP
Nonstop3h 13m
Sun Country Air
Sun 4/126:24 am
MSP
- BOS
Nonstop2h 48m
Sun Country Air
Deal found 1/16![Sun Country Air logo]()
$203
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 18, 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
Tue 3/24
7:16 am-9:22 am
Nonstop3h 06m
Chicago O'Hare Intl
Tue 3/31
4:10 pm-7:41 pm
Nonstop2h 31m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 5/2
5:10 pm-7:17 pm
Nonstop3h 07m
Chicago O'Hare Intl
Sat 5/9
7:00 am-10:28 am
Nonstop2h 28m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 1/30
4:10 pm-6:19 pm
Nonstop3h 09m
Chicago O'Hare Intl
Sun 2/1
7:05 am-10:40 am
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/29
7:30 am-9:41 am
Nonstop3h 11m
Chicago O'Hare Intl
Fri 2/6
7:05 am-10:40 am
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Tue 3/17
12:07 pm-5:01 pm
1 stop5h 54m
Chicago O'Hare Intl
Wed 3/25
7:30 am-10:49 am
Nonstop2h 19m
$141
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/5
3:35 pm-5:43 pm
Nonstop3h 08m
Chicago O'Hare Intl
Mon 2/9
9:40 am-5:13 pm
1 stop6h 33m
$152
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Fri 2/27
6:00 am-8:00 am
Nonstop3h 00m
Chicago O'Hare Intl
Mon 3/2
4:15 pm-7:37 pm
Nonstop2h 22m
$156
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 6/13
8:10 pm-10:06 pm
Nonstop2h 56m
Chicago O'Hare Intl
Tue 6/16
10:10 am-1:40 pm
Nonstop2h 30m
$156
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 2/21
4:25 pm-6:30 pm
Nonstop3h 05m
Chicago O'Hare Intl
Sun 3/1
7:30 am-10:49 am
Nonstop2h 19m
$156
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 6/4
6:50 am-8:45 am
Nonstop2h 55m
Chicago O'Hare Intl
Tue 6/9
9:30 am-12:55 pm
Nonstop2h 25m
$157
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 18, 2026.
It’s optimal to fly from Boston to Wisconsin at noon. By choosing this option you can save up to 52% 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 17, 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 18, 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 (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 January 18, 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
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
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 18, 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% |