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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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 April 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(JetBlue)

One-way from

$59
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$328

Good round-trip deal

$217 or less

Good one-way deal

$123 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
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One-way flight from Wisconsin to Boston Logan Intl
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Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 22, 2025.

This JetBlue deal was found by Cheapflights users on 4/21. 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.
Wed 5/710:50 amORD - BOS
Nonstop2h 28mJetBlue
Thu 5/86:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 4/21$117
This American Airlines deal was found by Cheapflights users on 4/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/68:40 pmORD - BOS
Nonstop2h 40mAmerican Airlines
Wed 6/1111:46 amBOS - ORD
Nonstop2h 51mAmerican Airlines
Deal found 4/20$118
This Flightnetwork deal was found by Cheapflights users on 4/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1312:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Tue 5/203:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Deal found 4/20$121
This United Airlines deal was found by Cheapflights users on 4/21. 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.
Sat 5/312:25 pmORD - BOS
Nonstop2h 38mUnited Airlines
Mon 6/27:45 amBOS - ORD
Nonstop2h 58mUnited Airlines
Deal found 4/21$135
This Southwest deal was found by Cheapflights users on 4/21. 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.
Fri 6/64:00 pmORD - BOS
1 stop7h 05mSouthwest
Tue 6/108:30 amBOS - ORD
1 stop8h 55mSouthwest
Deal found 4/21$136
This CheapOair deal was found by Cheapflights users on 4/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Tue 5/133:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Deal found 4/22$154
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/317:00 amORD - BOS
Nonstop2h 25mDelta
Sat 6/711:25 amBOS - ORD
Nonstop2h 49mDelta
Deal found 4/21$177
This JetBlue deal was found by Cheapflights users on 4/22. 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.
Tue 5/64:43 pmMKE - BOS
Nonstop2h 16mJetBlue
Sat 5/103:13 pmBOS - MKE
Nonstop2h 41mJetBlue
Deal found 4/22$187
This CheapOair deal was found by Cheapflights users on 4/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/154:15 pmORD - BOS
1 stop7h 50mFrontier
Sat 5/178:00 amBOS - ORD
1 stop16h 32mFrontier
Deal found 4/21$191
This Delta deal was found by Cheapflights users on 4/22. 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.
Thu 5/87:40 pmMKE - BOS
Nonstop2h 19mDelta
Sat 5/101:35 pmBOS - MKE
Nonstop2h 40mDelta
Deal found 4/22$197
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Wed 5/219:20 amMSP - BOS
1 stop8h 23mAmerican Airlines
Tue 6/35:15 amBOS - MSP
1 stop9h 45mAmerican Airlines
Deal found 4/22$203
This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/96:54 amMSP - BOS
Nonstop2h 48mMultiple Airlines
Thu 5/1510:04 amBOS - MSP
1 stop6h 38mMultiple Airlines
Deal found 4/21$204

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 April 22, 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 5/7

10:50 am-2:18 pm

Nonstop2h 28m

Boston Logan Intl

Mon 5/12

6:00 am-8:00 am

Nonstop3h 00m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/6

8:40 pm-12:20 am

Nonstop2h 40m

Boston Logan Intl

Wed 6/11

11:46 am-1:37 pm

Nonstop2h 51m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/13

12:41 pm-11:29 pm

1 stop9h 48m

Boston Logan Intl

Tue 5/20

3:49 pm-11:04 pm

1 stop8h 15m

$121

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/31

2:25 pm-6:03 pm

Nonstop2h 38m

Boston Logan Intl

Mon 6/2

7:45 am-9:43 am

Nonstop2h 58m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/6

4:00 pm-12:05 am

1 stop7h 05m

Boston Logan Intl

Tue 6/10

8:30 am-4:25 pm

1 stop8h 55m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/10

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Tue 5/13

3:49 pm-11:04 pm

1 stop8h 15m

$154

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/31

7:00 am-10:25 am

Nonstop2h 25m

Boston Logan Intl

Sat 6/7

11:25 am-1:14 pm

Nonstop2h 49m

$177

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 5/6

4:43 pm-7:59 pm

Nonstop2h 16m

Boston Logan Intl

Sat 5/10

3:13 pm-4:54 pm

Nonstop2h 41m

$187

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/15

4:15 pm-1:05 am

1 stop7h 50m

Boston Logan Intl

Sat 5/17

8:00 am-11:32 pm

1 stop16h 32m

$191

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Thu 5/8

7:40 pm-10:59 pm

Nonstop2h 19m

Boston Logan Intl

Sat 5/10

1:35 pm-3:15 pm

Nonstop2h 40m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

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, 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 April 22, 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.

Rainfall in Boston by month

Plan your trip to Boston by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

Temperature in Boston by month

Plan your trip to Boston by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated April 22, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Wisconsin to Boston have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,906 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,683 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Entertainment

7.1

Crew

8.5

Food

7.1

Boarding

8.2

Comfort

7.9

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 JetBlue, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from American Airlines and Spirit 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 (89%), Republic Airways (89%) or KLM (87%) 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 $444 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 $113.

  • 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 Wisconsin?

Book flights to Wisconsin if you plan to visit one of these locations
Marlborough
Warwick
Cambridge
Waltham
Framingham
Chestnut Hill
Seekonk
Randolph
Brockton
Lowell
Woburn
Somerville
York Beach
Saco
Burlington
West Yarmouth
Smithfield
Lincoln
Salem
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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$34Average$258FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$154Average$292FlexibilityNo cancel feeOn-time62%
DeltaCheapest$165Average$436FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$176Average$425FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$449FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$211Average$365FlexibilityNo cancel feeOn-time63%

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