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Wisconsin

$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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
Mar 20 — Mar 271
Fri 3/20
Fri 3/27
1 adult, Economy
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Cheap 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 February 18, 2026.

This JetBlue deal was found by Cheapflights users on 2/14. 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.
Wed 4/16:05 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Sun 4/58:55 am
ORD
-
BOS
Nonstop2h 32m
JetBlue
Deal found 2/14$132
This American Airlines deal was found by Cheapflights users on 2/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:45 pm
BOS
-
ORD
Nonstop3h 16m
American Airlines
Tue 2/248:45 pm
ORD
-
BOS
Nonstop2h 14m
American Airlines
Deal found 2/14$133
This United Airlines deal was found by Cheapflights users on 2/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:20 am
BOS
-
ORD
Nonstop3h 00m
United Airlines
Tue 5/54:30 pm
ORD
-
BOS
1 stop4h 44m
United Airlines
Deal found 2/15$134
This Super.com deal was found by Cheapflights users on 2/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:00 am
BOS
-
ORD
Nonstop3h 10m
JetBlue
Tue 3/1010:00 am
ORD
-
BOS
Nonstop2h 20m
JetBlue
Deal found 2/16$135
This American Airlines deal was found by Cheapflights users on 2/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/95:31 pm
BOS
-
ORD
Nonstop3h 17m
American Airlines
Tue 3/107:40 pm
ORD
-
BOS
Nonstop2h 21m
American Airlines
Deal found 2/17$136
This Delta deal was found by Cheapflights users on 2/15. 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.
Sun 4/127:25 am
BOS
-
ORD
Nonstop3h 10m
Delta
Tue 4/1410:15 am
ORD
-
BOS
Nonstop2h 20m
Delta
Deal found 2/15$137
This American Airlines deal was found by Cheapflights users on 2/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:35 pm
BOS
-
ORD
Nonstop3h 17m
American Airlines
Sun 4/126:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Deal found 2/14$138
This Expedia deal was found by Cheapflights users on 2/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:52 am
BOS
-
ORD
Nonstop2h 59m
Multiple Airlines
Thu 4/304:28 pm
ORD
-
BOS
1 stop7h 23m
Multiple Airlines
Deal found 2/16$139
This United Airlines deal was found by Cheapflights users on 2/16. 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.
Fri 4/37:00 am
BOS
-
ORD
Nonstop3h 00m
United Airlines
Sun 4/56:00 am
ORD
-
BOS
Nonstop2h 25m
United Airlines
Deal found 2/16$140
This United Airlines deal was found by Cheapflights users on 2/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:05 am
BOS
-
ORD
Nonstop3h 01m
United Airlines
Mon 5/186:00 am
ORD
-
BOS
Nonstop2h 25m
United Airlines
Deal found 2/17$141
This American Airlines deal was found by Cheapflights users on 2/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:52 am
BOS
-
ORD
Nonstop3h 11m
American Airlines
Sun 4/58:20 am
ORD
-
BOS
Nonstop2h 18m
American Airlines
Deal found 2/17$142
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Sat 5/95:40 am
BOS
-
ORD
1 stop16h 37m
Multiple Airlines
Tue 5/121:27 pm
ORD
-
BOS
1 stop9h 32m
Multiple Airlines
Deal found 2/16$143

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 February 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(JetBlue)

One-way from

$68
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$354

Good round-trip deal

$347 or less

Good one-way deal

$158 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. 14% potential increase in price ($56 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 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 4/28

4:55 pm-6:59 pm

Nonstop3h 04m

Chicago O'Hare Intl

Thu 4/30

6:50 am-10:11 am

Nonstop2h 21m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 3/7

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Wed 3/11

10:00 am-1:20 pm

Nonstop2h 20m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/7

7:15 am-9:25 am

Nonstop3h 10m

Chicago O'Hare Intl

Fri 4/10

7:35 pm-11:02 pm

Nonstop2h 27m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 5/1

7:26 pm-11:37 pm

1 stop5h 11m

Chicago O'Hare Intl

Mon 5/4

6:00 am-9:25 am

Nonstop2h 25m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/24

8:00 am-10:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Wed 3/25

6:45 am-2:24 pm

1 stop6h 39m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/12

7:15 am-9:25 am

Nonstop3h 10m

Chicago O'Hare Intl

Wed 3/25

7:35 pm-11:02 pm

Nonstop2h 27m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/28

4:25 pm-6:30 pm

Nonstop3h 05m

Chicago O'Hare Intl

Mon 3/2

4:14 pm-9:51 pm

1 stop4h 37m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/5

8:15 am-10:20 am

Nonstop3h 05m

Chicago O'Hare Intl

Mon 3/9

7:30 am-10:49 am

Nonstop2h 19m

$156

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 3/22

7:16 am-9:22 am

Nonstop3h 06m

Chicago O'Hare Intl

Thu 3/26

6:00 am-11:10 am

1 stop4h 10m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/2

4:15 pm-6:15 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sat 6/6

4:30 pm-8:03 pm

Nonstop2h 33m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/16

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 $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 February 18, 2026.

It’s optimal to fly from Boston to Wisconsin at noon. By choosing this option you can save up to 51% 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 February 7, 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.

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 February 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.
Southwest
8.0
Very good
4,294 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,208 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,313 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,304 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,900 reviews
Southwest
8.0
Very good
4,294 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 popular is this Boston to Wisconsin flight route?

    This flight path from Boston Logan Intl to Wisconsin was viewed by 1 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Boston to Wisconsin?

    There are many flights that can get you from Boston to Wisconsin in 3h 04m. Fly via Delta, JetBlue, or United Airlines 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?

    $78 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on American Airlines and Southwest, with prices starting from $88 and $98, 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 Delta (91%), Republic Airways (88%) and KLM (88%).

  • What are the cheapest flights from Boston to Wisconsin?

    Looking for the cheapest flight from Boston to Wisconsin? While on average our users pay $333, our data indicates the cheapest price to be $134. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $81.

  • 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 $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.

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 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 February 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$99Average$280FlexibilityNo cancel feeOn-time62%
DeltaCheapest$138Average$429FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$273FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$196Average$428FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$202Average$436FlexibilityNo cancel feeOn-time69%

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