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$59+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
1 adult, Economy
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Find flight deals from Boston to Wisconsin

Cheapest flights from Boston to Wisconsin
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 November 16, 2025.

This JetBlue deal was found by Cheapflights users on 11/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:30 amBOS - ORD
Nonstop3h 05mJetBlue
Thu 12/411:25 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 11/16$117
This JetBlue deal was found by Cheapflights users on 11/14. 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.
Sat 11/222:35 pmBOS - ORD
Nonstop3h 00mJetBlue
Mon 11/248:25 pmORD - BOS
Nonstop2h 32mJetBlue
Deal found 11/14$119
This JetBlue deal was found by Cheapflights users on 11/13. 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.
Thu 12/115:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Mon 12/158:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 11/13$122
This American Airlines deal was found by Cheapflights users on 11/13. 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 12/136:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Sun 12/147:00 amORD - BOS
Nonstop2h 29mAmerican Airlines
Deal found 11/13$123
This Frontier deal was found by Cheapflights users on 11/14. 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 12/1111:28 amBOS - ORD
1 stop11h 56mFrontier
Sun 12/146:00 amORD - BOS
1 stop5h 02mFrontier
Deal found 11/14$124
This United Airlines deal was found by Cheapflights users on 11/14. 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 12/56:23 pmBOS - ORD
Nonstop3h 00mUnited Airlines
Sun 12/77:30 amORD - BOS
Nonstop2h 19mUnited Airlines
Deal found 11/14$127
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/711:28 amBOS - ORD
1 stop11h 56mFrontier
Wed 1/218:10 amORD - BOS
1 stop15h 53mFrontier
Deal found 11/15$128
This American Airlines deal was found by Cheapflights users on 11/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Sat 12/208:53 pmORD - BOS
Nonstop2h 27mAmerican Airlines
Deal found 11/15$129
This Priceline deal was found by Cheapflights users on 11/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1511:23 amBOS - ORD
1 stop7h 04mMultiple Airlines
Tue 12/163:26 pmORD - BOS
1 stop7h 30mMultiple Airlines
Deal found 11/15$130
This Sun Country Air deal was found by Cheapflights users on 11/14. 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 12/711:42 amBOS - MSP
Nonstop3h 18mSun Country Air
Thu 12/116:54 amMSP - BOS
Nonstop2h 47mSun Country Air
Deal found 11/14$188
This Sun Country Air deal was found by Cheapflights users on 11/14. 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.
Mon 11/2411:42 amBOS - MSP
Nonstop3h 18mSun Country Air
Tue 11/255:42 amMSP - BOS
Nonstop2h 47mSun Country Air
Deal found 11/14$198
This Kiwi.com deal was found by Cheapflights users on 11/14. 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 12/411:42 amBOS - MSP
Nonstop3h 18mMultiple Airlines
Sat 12/67:00 amMSP - BOS
2 stops26h 22mMultiple Airlines
Deal found 11/14$199

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 November 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(JetBlue)

One-way from

$59
(Priceline)

Popular in

November

Cheapest in

September

Average price

$502

Good round-trip deal

$319 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Milwaukee-Mitchell flights.
Search Deals
From Boston Logan Intl to Wisconsin
Search Deals
One-way flight from Boston Logan Intl to Wisconsin
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Wisconsin.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Wisconsin.
Search Deals

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 November 16, 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

Wed 1/21

3:35 pm-5:44 pm

Nonstop3h 09m

Chicago O'Hare Intl

Mon 1/26

7:45 am-11:10 am

Nonstop2h 25m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 12/8

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Thu 12/11

8:38 pm-12:06 am

Nonstop2h 28m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/5

3:35 pm-5:44 pm

Nonstop3h 09m

Chicago O'Hare Intl

Sun 2/8

7:45 am-11:10 am

Nonstop2h 25m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/7

3:35 pm-5:44 pm

Nonstop3h 09m

Chicago O'Hare Intl

Mon 2/9

7:45 am-11:10 am

Nonstop2h 25m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 12/6

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Mon 12/8

8:38 pm-12:06 am

Nonstop2h 28m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/11

5:29 pm-7:43 pm

Nonstop3h 14m

Chicago O'Hare Intl

Mon 12/15

8:38 pm-12:06 am

Nonstop2h 28m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/5

6:23 pm-8:23 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 12/7

7:30 am-10:49 am

Nonstop2h 19m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/8

7:55 pm-10:01 pm

Nonstop3h 06m

Chicago O'Hare Intl

Sat 1/17

7:05 am-10:40 am

Nonstop2h 35m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/3

9:40 am-11:40 am

Nonstop3h 00m

Chicago O'Hare Intl

Fri 12/5

1:55 pm-5:15 pm

Nonstop2h 20m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 11/22

5:35 pm-7:50 pm

Nonstop3h 15m

Chicago O'Hare Intl

Mon 11/24

8:25 pm-11:57 pm

Nonstop2h 32m

$127

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/15

Showing 1-10 of 60 results
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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 $274). 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 November 16, 2025.

It’s optimal to fly from Boston to Wisconsin at noon. By choosing this option you can save up to 22% 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 16, 2024.

Travelers seeking maximum savings on their Boston to Wisconsin flight should consider departing on Sunday mornings 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 November 16, 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.
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,015 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,050 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,904 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • What airport do you fly from for flights from Boston to Wisconsin?

    For a flight from Boston to Wisconsin, you will be flying from Logan Intl. Boston Logan Intl (BOS) is just 2.6 mi from the center of the city.

  • How long is the flight from Boston to Wisconsin?

    There are many flights that can get you from Boston to Wisconsin in 3h 09m. Fly via JetBlue, Sun Country Air, or Southwest to get the fastest option. Airlines will cover a distance of 864 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Boston to Wisconsin one-way?

    $64 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on JetBlue and Frontier, with prices starting from $64 and $100, respectively.

  • What are the most popular routes from Boston to Wisconsin?

    While some choose either Boston Logan Intl - Minneapolis St Paul or Boston Logan Intl - Milwaukee-Mitchell, Boston Logan Intl - Chicago O'Hare Intl is the most popular route from Boston to Wisconsin.

  • What are the most reliable airlines from Boston to Wisconsin?

    The top 3 most reliable airlines when flying from Boston to Wisconsin are JetBlue (91%), EL AL (73%) and Delta (63%).

  • What are the cheapest flights from Boston to Wisconsin?

    Looking for the cheapest flight from Boston to Wisconsin? While on average our users pay $325, our data indicates the cheapest price to be $148. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $71.

  • Can I find deals for flights from Boston to Wisconsin that include hotel bookings?

    Yes. In addition to deals on Boston to Wisconsin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Wisconsin?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Wisconsin.

  • Can I find deals for business class flights from Boston to Wisconsin?

    Yes. Cheapflights offers flight deals from Boston to Wisconsin by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $274). 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.

See more FAQs

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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.
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Top 6 airlines flying from Boston to Wisconsin

Discover the top 6 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 November 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$294FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$145Average$187FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$292FlexibilityNo cancel feeOn-time63%
DeltaCheapest$186Average$482FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$196Average$444FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$202Average$446FlexibilityNo cancel feeOn-time69%

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