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$60+ 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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
nov. 22 — nov. 291
sáb. 11/22
sáb. 11/29
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 octubre 23, 2025.

This United Airlines deal was found by Cheapflights users on 10/21. 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.
lun. 12/229:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
jue. 12/256:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 10/21$120
This American Airlines deal was found by Cheapflights users on 10/22. 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.
mié. 10/298:25 pmORD - BOS
Nonstop2h 29mAmerican Airlines
sáb. 11/17:00 amBOS - ORD
Nonstop3h 13mAmerican Airlines
Deal found 10/22$122
This Southwest deal was found by Cheapflights users on 10/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/101:45 pmORD - BOS
1 stop7h 30mSouthwest
dom. 12/145:00 amBOS - ORD
1 stop8h 15mSouthwest
Deal found 10/21$123
This JetBlue deal was found by Cheapflights users on 10/23. 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.
sáb. 11/810:00 amORD - BOS
Nonstop2h 17mJetBlue
lun. 11/108:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/23$125
This American Airlines deal was found by Cheapflights users on 10/23. 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.
lun. 12/157:00 amORD - BOS
Nonstop2h 29mAmerican Airlines
jue. 1/15:30 pmBOS - ORD
Nonstop3h 14mAmerican Airlines
Deal found 10/23$126
This Delta deal was found by Cheapflights users on 10/22. 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. 12/48:55 amORD - BOS
1 stop6h 08mDelta
dom. 12/712:50 pmBOS - ORD
Nonstop2h 57mDelta
Deal found 10/22$127
This American Airlines deal was found by Cheapflights users on 10/23. 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.
mar. 12/25:00 pmORD - BOS
Nonstop2h 22mAmerican Airlines
mié. 12/36:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Deal found 10/23$128
This Kiwi.com deal was found by Cheapflights users on 10/22. 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. 12/34:01 pmORD - BOS
1 stop17h 21mFrontier
lun. 12/811:23 amBOS - ORD
1 stop7h 04mFrontier
Deal found 10/22$130
This Delta deal was found by Cheapflights users on 10/23. 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.
vie. 12/55:59 pmORD - BOS
1 stop6h 28mDelta
dom. 12/74:05 pmBOS - ORD
Nonstop2h 57mDelta
Deal found 10/23$131
This JetBlue deal was found by Cheapflights users on 10/22. 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. 12/317:41 pmORD - BOS
Nonstop2h 29mJetBlue
dom. 1/44:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 10/22$132
This American Airlines deal was found by Cheapflights users on 10/22. 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.
vie. 12/128:40 pmORD - BOS
Nonstop2h 33mAmerican Airlines
mié. 12/176:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Deal found 10/22$133
This JetBlue deal was found by Cheapflights users on 10/21. 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. 11/66:55 pmORD - BOS
Nonstop2h 32mJetBlue
mar. 11/113:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 10/21$135

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 octubre 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$120
(United Airlines)

One-way from

$60
(Southwest)

Popular in

December

Cheapest in

September

Average price

$277

Good round-trip deal

$238 or less

Good one-way deal

$208 or less
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
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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. 17% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
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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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 octubre 23, 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

mié. 11/5

6:45 am-3:00 pm

1 stop7h 15m

Boston Logan Intl

mié. 11/12

8:30 am-10:35 am

Nonstop3h 05m

$125

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 11/6

7:45 am-2:55 pm

1 stop6h 10m

Boston Logan Intl

mié. 11/12

3:55 pm-5:55 pm

Nonstop3h 00m

$125

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 11/5

6:55 pm-10:27 pm

Nonstop2h 32m

Boston Logan Intl

lun. 11/10

3:55 pm-5:55 pm

Nonstop3h 00m

$125

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 12/6

4:05 pm-12:01 am

1 stop6h 56m

Boston Logan Intl

dom. 12/7

12:50 pm-2:47 pm

Nonstop2h 57m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 12/4

6:45 am-11:59 am

1 stop4h 14m

Boston Logan Intl

dom. 12/7

4:05 pm-6:02 pm

Nonstop2h 57m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 11/14

7:15 pm-10:46 pm

Nonstop2h 31m

Boston Logan Intl

lun. 11/17

7:55 pm-9:53 pm

Nonstop2h 58m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

lun. 12/15

9:40 am-5:25 pm

1 stop6h 45m

Boston Logan Intl

jue. 1/1

5:45 am-11:50 am

1 stop7h 05m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 11/6

10:25 am-1:55 pm

Nonstop2h 30m

Boston Logan Intl

lun. 11/10

4:05 pm-6:13 pm

Nonstop3h 08m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 1/9

5:50 am-12:38 pm

1 stop5h 48m

Boston Logan Intl

dom. 1/11

5:30 am-9:35 am

1 stop5h 05m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 11/13

7:15 am-12:28 pm

1 stop4h 13m

Boston Logan Intl

dom. 11/16

6:00 am-8:00 am

Nonstop3h 00m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/22

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 January is currently the most expensive (average of $221). 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 octubre 23, 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 43% 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.

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 $184, JetBlue can have you in Boston from Wisconsin in 4h 35m. Airlines will cover a distance of 857 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 United Airlines, with whom users have recently found tickets for as low as $64. However, be on the lookout for offers from Delta and Southwest, 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 (70%), Republic Airways (70%) or KLM (60%) 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 $906 for a flight from Wisconsin to Boston. The cheapest flight overall is $103 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $91.

  • 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 January is currently the most expensive (average of $221). 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 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 octubre 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$276FlexibilityNo cancel feeOn-time62%
DeltaCheapest$152Average$416FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$164Average$258FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$176Average$266FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$177Average$423FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$405FlexibilityNo cancel feeOn-time69%

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