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$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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MKE
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
1 adult, Economy
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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 agosto 20, 2025.

Round-trip from

$132
(Delta)

One-way from

$68
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$292

Good round-trip deal

$212 or less

Good one-way deal

$158 or less
From Boston Logan Intl to Wisconsin
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One-way flight from Boston Logan Intl to Wisconsin
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Highest demand for flights based on searches. 17% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Wisconsin.
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Price to beat on a one-way flight from Boston Logan Intl to Wisconsin.
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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 agosto 20, 2025.

This Delta deal was found by Cheapflights users on 8/19. 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.
jue. 9/47:20 amBOS - ORD
Nonstop2h 55mDelta
dom. 9/77:00 amORD - BOS
Nonstop2h 30mDelta
Deal found 8/19$132
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/66:10 amBOS - ORD
1 stop12h 29mSpirit Airlines
mié. 9/1011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/18$135
This FlightHub deal was found by Cheapflights users on 8/19. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/42:53 pmBOS - ORD
1 stop8h 05mSpirit Airlines
mar. 9/911:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/19$136
This JetBlue deal was found by Cheapflights users on 8/18. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/247:00 amBOS - ORD
Nonstop2h 56mJetBlue
jue. 10/27:50 pmORD - BOS
Nonstop2h 35mJetBlue
Deal found 8/18$137
This American Airlines deal was found by Cheapflights users on 8/18. 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.
jue. 9/185:00 amBOS - ORD
Nonstop2h 51mAmerican Airlines
lun. 9/226:05 amORD - BOS
Nonstop2h 27mAmerican Airlines
Deal found 8/18$138
This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/86:49 pmBOS - ORD
1 stop17h 03mSpirit Airlines
mié. 9/1011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/19$139
This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/176:10 amBOS - ORD
1 stop17h 38mSpirit Airlines
mié. 9/2411:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/19$140
This CheapOair deal was found by Cheapflights users on 8/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/77:00 amBOS - ORD
Nonstop2h 56mJetBlue
sáb. 9/139:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 8/18$142
This FlightHub deal was found by Cheapflights users on 8/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/93:00 pmBOS - ORD
1 stop8h 48mMultiple Airlines
vie. 9/126:21 pmORD - BOS
1 stop12h 22mMultiple Airlines
Deal found 8/18$143
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/52:53 pmBOS - ORD
1 stop8h 05mSpirit Airlines
mar. 9/911:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/18$144
This lastminute.com deal was found by Cheapflights users on 8/18. 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 lastminute.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/184:30 pmBOS - ORD
1 stop5h 19mJetBlue
lun. 9/227:50 pmORD - BOS
Nonstop2h 35mJetBlue
Deal found 8/18$145
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
mié. 9/173:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
sáb. 9/2011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/19$146

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 agosto 20, 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

vie. 9/5

7:55 pm-9:56 pm

Nonstop3h 01m

Chicago O'Hare Intl

dom. 9/7

7:00 am-10:30 am

Nonstop2h 30m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 10/4

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

lun. 10/6

6:50 pm-10:23 pm

Nonstop2h 33m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 10/24

8:47 pm-10:35 pm

Nonstop2h 48m

Chicago O'Hare Intl

dom. 10/26

6:15 am-9:30 am

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 11/29

5:35 pm-7:50 pm

Nonstop3h 15m

Chicago O'Hare Intl

mié. 12/3

11:30 am-2:46 pm

Nonstop2h 16m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 10/4

7:25 am-9:15 am

Nonstop2h 50m

Chicago O'Hare Intl

mié. 10/8

7:05 am-10:29 am

Nonstop2h 24m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 9/22

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

sáb. 9/27

9:51 am-1:20 pm

Nonstop2h 29m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 9/10

7:20 am-9:15 am

Nonstop2h 55m

Chicago O'Hare Intl

sáb. 9/13

7:25 am-10:55 am

Nonstop2h 30m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 9/9

7:20 am-9:15 am

Nonstop2h 55m

Chicago O'Hare Intl

mar. 9/16

7:25 am-10:55 am

Nonstop2h 30m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 9/15

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

mar. 9/23

9:51 am-1:20 pm

Nonstop2h 29m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

lun. 9/22

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

mié. 10/1

7:50 pm-11:25 pm

Nonstop2h 35m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

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, February is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $280). Flying from Boston to Wisconsin in June is currently the most expensive (average of $376). 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 agosto 20, 2025.

When flying from Boston to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 agosto 20, 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
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
JetBlue
7.2
Good
2,916 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 2h 56m. 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?

    $69 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on United Airlines and Southwest, with prices starting from $69 and $89, 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 (77%), Republic Airways (77%) and JetBlue (72%).

  • What are the cheapest flights from Boston to Wisconsin?

    Looking for the cheapest flight from Boston to Wisconsin? While on average our users pay $289, our data indicates the cheapest price to be $88. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $107.

  • 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, February is the cheapest month in which you can book a flight from Boston to Wisconsin (average of $280). Flying from Boston to Wisconsin in June is currently the most expensive (average of $376). 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.

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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 agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$112Average$187FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$123Average$297FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$307FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$484FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$196Average$455FlexibilityNo cancel feeOn-time71%
DeltaCheapest$200Average$502FlexibilityNo cancel feeOn-timeN/A

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