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$68+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Mar 13 — Mar 201
Fri 3/13
Fri 3/20
1 adult, Economy
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Cheap 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 February 11, 2026.

This United Airlines deal was found by Cheapflights users on 2/9. 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 5/89:30 pm
ORD
-
BOS
Nonstop2h 29m
United Airlines
Sun 5/106:00 am
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 2/9$131
This Flysmarter deal was found by Cheapflights users on 2/9. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:41 pm
ORD
-
BOS
1 stop6h 17m
JetBlue
Sun 3/87:00 am
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 2/9$133
This Super.com deal was found by Cheapflights users on 2/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/1510:00 am
ORD
-
BOS
Nonstop2h 20m
JetBlue
Wed 3/47:00 am
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 2/9$134
This JetBlue deal was found by Cheapflights users on 2/8. 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 2/1510:00 am
ORD
-
BOS
Nonstop2h 20m
JetBlue
Thu 2/197:00 am
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 2/8$135
This JetBlue deal was found by Cheapflights users on 2/9. 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 2/2410:00 am
ORD
-
BOS
Nonstop2h 20m
JetBlue
Wed 3/117:00 am
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 2/9$136
This American Airlines deal was found by Cheapflights users on 2/9. 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 4/106:00 am
ORD
-
BOS
Nonstop2h 27m
American Airlines
Sun 4/127:40 pm
BOS
-
ORD
Nonstop3h 10m
American Airlines
Deal found 2/9$137
This Expedia deal was found by Cheapflights users on 2/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1410:00 am
ORD
-
BOS
Nonstop2h 20m
Multiple Airlines
Tue 3/36:00 am
BOS
-
ORD
1 stop11h 52m
Multiple Airlines
Deal found 2/7$138
This Priceline deal was found by Cheapflights users on 2/7. 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.
Thu 2/264:42 pm
ORD
-
BOS
1 stop7h 31m
Multiple Airlines
Thu 3/57:00 am
BOS
-
ORD
Nonstop3h 10m
Multiple Airlines
Deal found 2/7$139
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:00 am
ORD
-
BOS
1 stop9h 15m
Spirit Airlines
Tue 3/249:45 am
BOS
-
ORD
1 stop8h 11m
Spirit Airlines
Deal found 2/11$140
This Cheapflightsfares deal was found by Cheapflights users on 2/8. 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.
Fri 3/66:04 am
ORD
-
BOS
1 stop7h 05m
JetBlue
Sun 3/87:00 am
BOS
-
ORD
Nonstop3h 10m
JetBlue
Deal found 2/8$141
This Southwest deal was found by Cheapflights users on 2/8. 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.
Thu 3/122:40 pm
ORD
-
BOS
1 stop9h 05m
Southwest
Wed 3/188:20 am
BOS
-
ORD
1 stop5h 30m
Southwest
Deal found 2/8$142
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:20 pm
MKE
-
BOS
1 stop5h 53m
Frontier
Thu 3/511:45 am
BOS
-
MKE
1 stop7h 57m
Frontier
Deal found 2/10$179

Find flight deals from Wisconsin to Boston

Keep the following information in mind while searching for Wisconsin to Boston flight deals. Data was last updated February 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$131
(United Airlines)

One-way from

$68
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$321

Good round-trip deal

$297 or less

Good one-way deal

$234 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. 6% potential increase in price ($24 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 February 2026
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 February 11, 2026.
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 7/8

6:04 pm-9:40 pm

Nonstop2h 36m

Boston Logan Intl

Mon 7/13

6:00 am-7:58 am

Nonstop2h 58m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/26

9:26 pm-12:59 am

Nonstop2h 33m

Boston Logan Intl

Tue 6/30

8:05 pm-10:05 pm

Nonstop3h 00m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/26

9:26 pm-12:59 am

Nonstop2h 33m

Boston Logan Intl

Wed 7/1

7:10 am-9:08 am

Nonstop2h 58m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/2

6:00 am-9:25 am

Nonstop2h 25m

Boston Logan Intl

Mon 4/6

7:00 am-9:00 am

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 3/4

6:04 am-2:16 pm

1 stop7h 12m

Boston Logan Intl

Wed 3/11

7:00 am-9:10 am

Nonstop3h 10m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/6

6:04 am-2:35 pm

1 stop7h 31m

Boston Logan Intl

Wed 3/11

7:00 am-9:10 am

Nonstop3h 10m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 3/10

6:04 am-2:45 pm

1 stop7h 41m

Boston Logan Intl

Wed 3/11

7:00 am-9:10 am

Nonstop3h 10m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 3/7

12:59 pm-8:23 pm

1 stop6h 24m

Boston Logan Intl

Mon 3/9

7:00 am-9:10 am

Nonstop3h 10m

$143

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 3/9

7:35 pm-11:02 pm

Nonstop2h 27m

Boston Logan Intl

Sun 3/15

7:25 am-9:35 am

Nonstop3h 10m

$147

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/1

9:30 pm-12:59 am

Nonstop2h 29m

Boston Logan Intl

Sun 5/3

5:45 am-9:37 am

1 stop4h 52m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

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, September is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $93). Flying from Wisconsin to Boston in December is currently the most expensive (average of $217). 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 February 11, 2026.

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 47% 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 February 7, 2026.

Travelers seeking maximum savings on their Wisconsin to Boston flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon 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 $135, United Airlines can have you in Boston from Wisconsin in 2h 36m. 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 $78. However, be on the lookout for offers from American Airlines 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 KLM (81%), Republic Airways (74%) or Scandinavian Airlines (72%) 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 $348 for a flight from Wisconsin to Boston. The cheapest flight overall is $119 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $107.

  • 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, September is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $93). Flying from Wisconsin to Boston in December is currently the most expensive (average of $217). 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
Medford
Cambridge
Hampton Beach
Watertown
Seekonk
Brockton
Concord
Seabrook
Cranston
Lincoln
Warwick
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell

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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 February 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$92Average$270FlexibilityNo cancel feeOn-time62%
DeltaCheapest$106Average$369FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$260FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$396FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$186Average$388FlexibilityNo cancel feeOn-time69%

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