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$59+ 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 2/16. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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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 November 21, 2025.

This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/105:12 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Wed 12/176:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Deal found 11/19$117
This JetBlue deal was found by Cheapflights users on 11/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:25 amORD - BOS
Nonstop2h 24mJetBlue
Sun 12/148:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/19$122
This Trip.com deal was found by Cheapflights users on 11/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Thu 12/115:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Deal found 11/19$125
This Trip.com deal was found by Cheapflights users on 11/19. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:38 pmORD - BOS
Nonstop2h 28mJetBlue
Sun 12/75:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Deal found 11/19$126
This JetBlue deal was found by Cheapflights users on 11/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:38 pmORD - BOS
Nonstop2h 28mJetBlue
Mon 12/155:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Deal found 11/19$127
This JetBlue deal was found by Cheapflights users on 11/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/217:41 pmORD - BOS
Nonstop2h 29mJetBlue
Sat 12/275:00 pmBOS - ORD
Nonstop3h 20mJetBlue
Deal found 11/19$131
This United Airlines deal was found by Cheapflights users on 11/20. 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 12/119:19 amORD - BOS
Nonstop2h 24mUnited Airlines
Wed 1/79:30 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/20$132
This United Airlines deal was found by Cheapflights users on 11/20. 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 12/187:45 amORD - BOS
Nonstop2h 22mUnited Airlines
Wed 1/712:45 pmBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/20$134
This United Airlines deal was found by Cheapflights users on 11/20. 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 12/279:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Fri 1/26:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/20$137
This Priceline deal was found by Cheapflights users on 11/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/103:26 pmORD - BOS
1 stop7h 30mMultiple Airlines
Thu 12/1111:28 amBOS - ORD
1 stop6h 59mMultiple Airlines
Deal found 11/19$138
This Sun Country Air deal was found by Cheapflights users on 11/19. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:54 amMSP - BOS
Nonstop2h 57mSun Country Air
Sun 12/286:45 amBOS - MSP
Nonstop3h 11mSun Country Air
Deal found 11/19$193
This Priceline deal was found by Cheapflights users on 11/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:54 amMSP - BOS
Nonstop2h 57mSun Country Air
Sun 12/286:45 amBOS - MSP
Nonstop3h 11mSun Country Air
Deal found 11/19$197

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 November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(JetBlue)

One-way from

$59
(United Airlines)

Popular in

December

Cheapest in

May

Average price

$438

Good round-trip deal

$319 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
Search Deals
From Wisconsin to Boston Logan Intl
Search Deals
One-way flight from Wisconsin to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 24% potential increase in price ($108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 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 Wisconsin to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Wisconsin to Boston Logan Intl.
Search Deals

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 November 21, 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

Wed 11/26

12:50 pm-4:18 pm

Nonstop2h 28m

Boston Logan Intl

Sat 11/29

5:15 pm-7:27 pm

Nonstop3h 12m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/3

4:05 pm-7:25 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

6:00 am-8:00 am

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/23

9:12 pm-12:45 am

Nonstop2h 33m

Boston Logan Intl

Thu 1/8

12:45 pm-2:49 pm

Nonstop3h 04m

$134

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/8

11:00 am-2:28 pm

Nonstop2h 28m

Boston Logan Intl

Fri 1/9

7:30 am-9:41 am

Nonstop3h 11m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/31

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Tue 2/3

7:30 am-9:41 am

Nonstop3h 11m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/28

9:12 pm-12:45 am

Nonstop2h 33m

Boston Logan Intl

Mon 1/5

7:45 am-9:49 am

Nonstop3h 04m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/17

4:05 pm-7:25 pm

Nonstop2h 20m

Boston Logan Intl

Tue 12/30

7:45 am-9:49 am

Nonstop3h 04m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/21

6:45 am-2:12 pm

1 stop6h 27m

Boston Logan Intl

Sat 12/27

5:00 pm-7:20 pm

Nonstop3h 20m

$149

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/28

7:41 pm-11:10 pm

Nonstop2h 29m

Boston Logan Intl

Fri 1/2

2:55 pm-10:04 pm

1 stop8h 09m

$149

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/15

7:45 am-11:10 am

Nonstop2h 25m

Boston Logan Intl

Mon 1/19

12:15 pm-7:45 pm

1 stop8h 30m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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, October is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $88). Flying from Wisconsin to Boston in December is currently the most expensive (average of $246). 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 November 21, 2025.

A simple way to save on the total cost of your ticket is to fly from Wisconsin to Boston in the evening. If you’re flexible enough to do this you can expect to save up to 44% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Wisconsin to Boston?

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to Boston. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to Boston flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Wisconsin to Boston?

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 $127, JetBlue can have you in Boston from Wisconsin in 2h 20m. Airlines will cover a distance of 864 mi. Generally, flights for this route are nonstop.

  • 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 $59. However, be on the lookout for offers from United Airlines and Delta, 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 EL AL (58%), Virgin Atlantic (56%) or KLM (53%) 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 $915 for a flight from Wisconsin to Boston. The cheapest flight overall is $138 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $111.

  • 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, October is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $88). Flying from Wisconsin to Boston in December is currently the most expensive (average of $246). 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
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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Top 5 airlines flying from Wisconsin to Boston

Discover the top 5 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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$277FlexibilityNo cancel feeOn-time62%
DeltaCheapest$152Average$415FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$257FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$427FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$192Average$399FlexibilityNo cancel feeOn-time69%

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