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$69+ Cheap flights from Wisconsin to Boston (BOS)

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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Wisconsin to Boston

Keep the following information in mind while searching for Wisconsin to Boston flight deals. Data was last updated August 14, 2025.

Round-trip from

$135
(Kiwi.com)

One-way from

$69
(United Airlines)

Popular in

December

Cheapest in

August

Average price

$254

Good round-trip deal

$236 or less

Good one-way deal

$123 or less
From Wisconsin to Boston Logan Intl
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One-way flight from Wisconsin to Boston Logan Intl
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Highest demand for flights based on searches. 13% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 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 Wisconsin to Boston Logan Intl.
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Price to beat on a one-way flight from Wisconsin to Boston Logan Intl.
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Find flight deals from Wisconsin to Boston

Cheapest flights from Wisconsin to Boston
Explore the most affordable flight options available from Wisconsin to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/14. 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.
Tue 9/1611:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Tue 9/2312:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Deal found 8/14$135
This FlightHub deal was found by Cheapflights users on 8/12. 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.
Wed 9/311:36 amORD - BOS
1 stop11h 13mSpirit Airlines
Sat 9/63:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Deal found 8/12$136
This Delta deal was found by Cheapflights users on 8/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/172:05 pmORD - BOS
Nonstop2h 39mDelta
Fri 9/197:30 pmBOS - ORD
Nonstop2h 45mDelta
Deal found 8/14$137
This JetBlue deal was found by Cheapflights users on 8/12. 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.
Fri 9/197:50 pmORD - BOS
Nonstop2h 35mJetBlue
Sun 9/217:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 8/12$138
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/59:37 pmORD - BOS
Nonstop2h 32mUnited Airlines
Sun 9/75:30 amBOS - ORD
1 stop5h 06mUnited Airlines
Deal found 8/12$139
This CheapOair deal was found by Cheapflights users on 8/12. 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.
Wed 10/156:00 amORD - BOS
1 stop6h 44mSpirit Airlines
Wed 10/226:11 amBOS - ORD
1 stop13h 13mSpirit Airlines
Deal found 8/12$140
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Sun 8/249:15 pmORD - BOS
Nonstop2h 30mUnited Airlines
Tue 9/211:00 amBOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 8/12$142
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/911:57 amORD - BOS
1 stop11h 00mMultiple Airlines
Fri 9/1210:53 amBOS - ORD
1 stop14h 17mMultiple Airlines
Deal found 8/14$143
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/611:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Wed 9/103:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Deal found 8/12$146
This Delta deal was found by Cheapflights users on 8/12. 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.
Thu 10/167:05 amORD - BOS
Nonstop2h 24mDelta
Wed 10/227:30 pmBOS - ORD
Nonstop2h 49mDelta
Deal found 8/12$147
This JetBlue deal was found by Cheapflights users on 8/12. 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 10/76:50 pmORD - BOS
Nonstop2h 33mJetBlue
Wed 10/87:00 amBOS - ORD
Nonstop2h 57mJetBlue
Deal found 8/12$148
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/911:13 amORD - BOS
2 stops10h 57mSpirit Airlines
Wed 9/173:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Deal found 8/11$150

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Boston 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 August 14, 2025.
Use the filters below to find and compare flights from Wisconsin to Boston that are best for you.

Fly from

Wisconsin

Fly to

Boston

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/27

2:00 pm-5:39 pm

Nonstop2h 39m

Boston Logan Intl

Sat 10/4

5:05 pm-7:05 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 10/1

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

Tue 10/7

7:00 am-8:57 am

Nonstop2h 57m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

2:05 pm-5:44 pm

Nonstop2h 39m

Boston Logan Intl

Fri 9/19

7:30 pm-9:15 pm

Nonstop2h 45m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 10/6

6:50 pm-10:23 pm

Nonstop2h 33m

Boston Logan Intl

Tue 10/7

7:00 am-8:57 am

Nonstop2h 57m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/26

7:00 am-10:29 am

Nonstop2h 29m

Boston Logan Intl

Wed 8/27

7:55 pm-9:54 pm

Nonstop2h 59m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/17

6:50 pm-10:23 pm

Nonstop2h 33m

Boston Logan Intl

Wed 10/22

4:05 pm-5:55 pm

Nonstop2h 50m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/26

7:00 am-10:29 am

Nonstop2h 29m

Boston Logan Intl

Fri 9/5

7:55 pm-9:56 pm

Nonstop3h 01m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/3

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

Sat 10/4

7:00 am-8:56 am

Nonstop2h 56m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/11

10:15 am-1:49 pm

Nonstop2h 34m

Boston Logan Intl

Thu 9/18

4:05 pm-5:59 pm

Nonstop2h 54m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/20

9:51 am-1:20 pm

Nonstop2h 29m

Boston Logan Intl

Sun 9/21

7:00 am-8:56 am

Nonstop2h 56m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Wisconsin 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 Wisconsin to Boston

What is the cheapest month to book a flight from Wisconsin to Boston?

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $218). Flying from Wisconsin to Boston in July is currently the most expensive (average of $311). 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 WI to BOS?

Find hourly flight availability from Wisconsin to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to Boston as you normally would.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Boston. 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 into for flights to Boston from Wisconsin?

    Located just 2.6 mi from the city center, Boston Logan Intl (BOS) is the airport most travelers will use when flying to Boston from Wisconsin.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Spirit Airlines and American Airlines, as they are both options that can get you from Wisconsin to Boston for a low price.

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

    Most travelers choose Chicago O'Hare Intl - Boston Logan Intl, Minneapolis St Paul - Boston Logan Intl or Milwaukee-Mitchell - Boston Logan Intl when deciding on the best route from Wisconsin to Boston.

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

    No one likes to see their flight delayed. When booking a flight from Wisconsin to Boston consider choosing Air France (100%), Delta (74%) or Republic Airways (74%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Wisconsin to Boston?

    On average you can expect to pay $297 for a flight from Wisconsin to Boston. The cheapest flight overall is $78 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $99.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Wisconsin to Boston 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 Wisconsin to Boston?

    Currently, January is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $218). Flying from Wisconsin to Boston in July is currently the most expensive (average of $311). 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Watertown
Hampton Beach
Waltham
Seabrook
Lowell
Lincoln
Smithfield
Cranston
Chestnut Hill
Warwick
Peabody
Quincy
York Beach
Chelsea
Swansea
Saugus
Burlington
Braintree

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Top 6 airlines flying from Wisconsin to Boston

Discover the top 6 airlines that operate flights from Wisconsin to Boston. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$128Average$286FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$164Average$267FlexibilityNo cancel feeOn-time65%
DeltaCheapest$167Average$433FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$417FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$428FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$186Average$300FlexibilityNo cancel feeOn-time63%

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