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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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
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 septiembre 17, 2025.

Round-trip from

$127
(United Airlines)

One-way from

$69
(JetBlue)

Popular in

December

Cheapest in

August

Average price

$277

Good round-trip deal

$180 or less

Good one-way deal

$266 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. 15% potential increase in price ($57 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 September 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 septiembre 17, 2025.

This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/297:50 pmORD - BOS
Nonstop2h 35mJetBlue
sáb. 10/47:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/15$127
This JetBlue deal was found by Cheapflights users on 9/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/19:51 amORD - BOS
Nonstop2h 29mJetBlue
mié. 10/14:40 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 9/15$130
This JetBlue deal was found by Cheapflights users on 9/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/249:51 amORD - BOS
Nonstop2h 29mJetBlue
mié. 10/157:09 amBOS - ORD
Nonstop3h 13mJetBlue
Deal found 9/17$132
This United Airlines deal was found by Cheapflights users on 9/16. 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.
vie. 11/79:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
lun. 11/106:23 pmBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 9/16$133
This JetBlue deal was found by Cheapflights users on 9/17. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/611:20 amORD - BOS
Nonstop2h 24mJetBlue
lun. 11/108:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 9/17$135
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
mié. 10/86:00 amORD - BOS
1 stop6h 20mSpirit Airlines
mié. 10/156:16 amBOS - ORD
1 stop18h 29mSpirit Airlines
Deal found 9/15$136
This United Airlines deal was found by Cheapflights users on 9/15. 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.
mar. 9/232:15 pmORD - BOS
Nonstop2h 31mUnited Airlines
mar. 9/3011:02 amBOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 9/15$137
This United Airlines deal was found by Cheapflights users on 9/16. 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.
jue. 10/309:25 pmORD - BOS
Nonstop2h 20mUnited Airlines
sáb. 11/16:26 pmBOS - ORD
Nonstop2h 59mUnited Airlines
Deal found 9/16$138
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/286:00 amORD - BOS
1 stop6h 20mSpirit Airlines
mar. 10/283:00 pmBOS - ORD
1 stop11h 03mSpirit Airlines
Deal found 9/15$139
This Orbitz deal was found by Cheapflights users on 9/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/35:50 pmORD - BOS
1 stop12h 53mMultiple Airlines
mar. 10/73:00 pmBOS - ORD
1 stop9h 45mMultiple Airlines
Deal found 9/15$140
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sáb. 10/1811:55 amORD - BOS
1 stop11h 04mSpirit Airlines
mar. 10/283:00 pmBOS - ORD
1 stop11h 03mSpirit Airlines
Deal found 9/14$141
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
sáb. 10/1811:55 amORD - BOS
1 stop11h 04mSpirit Airlines
mar. 10/212:15 pmBOS - ORD
1 stop8h 18mSpirit Airlines
Deal found 9/16$142

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 septiembre 17, 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

mar. 10/7

7:13 pm-10:46 pm

Nonstop2h 33m

Boston Logan Intl

mié. 10/15

7:09 am-9:22 am

Nonstop3h 13m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 10/25

12:40 pm-10:15 pm

2 stops8h 35m

Boston Logan Intl

dom. 10/26

5:00 am-12:45 pm

1 stop8h 45m

$148

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 10/18

10:08 am-1:37 pm

Nonstop2h 29m

Boston Logan Intl

vie. 10/24

4:05 pm-6:18 pm

Nonstop3h 13m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 11/6

9:25 pm-12:45 am

Nonstop2h 20m

Boston Logan Intl

sáb. 11/15

6:00 am-10:45 am

1 stop5h 45m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 10/18

10:41 am-4:22 pm

1 stop4h 41m

Boston Logan Intl

sáb. 10/25

6:00 am-7:56 am

Nonstop2h 56m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 10/4

6:00 am-11:53 am

1 stop4h 53m

Boston Logan Intl

lun. 10/6

8:47 pm-10:35 pm

Nonstop2h 48m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 11/19

11:20 am-2:44 pm

Nonstop2h 24m

Boston Logan Intl

lun. 11/24

4:28 pm-10:50 pm

1 stop7h 22m

$163

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 11/19

10:30 am-1:59 pm

Nonstop2h 29m

Boston Logan Intl

lun. 11/24

7:50 pm-9:50 pm

Nonstop3h 00m

$167

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 10/29

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

lun. 11/3

7:30 pm-9:19 pm

Nonstop2h 49m

$167

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 10/7

10:08 am-1:37 pm

Nonstop2h 29m

Boston Logan Intl

mar. 10/14

7:00 am-12:22 pm

1 stop6h 22m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 septiembre 17, 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.

Weekly flight availability from Wisconsin to Boston

Explore weekly flight availability from Wisconsin to Boston. 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 septiembre 17, 2025.

The most flights from USWI to BOS are scheduled on a Monday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

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.

  • How popular is this Wisconsin to Boston flight route?

    Flights from Wisconsin to Boston Logan Intl have been viewed 7 times in the past calendar month.

  • How long is the flight from Wisconsin to Boston?

    For as low as $155, JetBlue can have you in Boston from Wisconsin in 2h 20m. Airlines will cover a distance of 864 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Southwest and United 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 Delta (81%), Republic Airways (81%) or Air France (76%) 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 $307 for a flight from Wisconsin to Boston. The cheapest flight overall is $88 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $117.

  • 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
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Old Orchard Beach
Brockton
Waltham

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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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$119Average$280FlexibilityNo cancel feeOn-time62%
DeltaCheapest$160Average$433FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$164Average$267FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$184Average$429FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$186Average$289FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$186Average$413FlexibilityNo cancel feeOn-time69%

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