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$88+ 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Aug 15 — Aug 221
Sat 8/15
Sat 8/22
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 July 16, 2026.

This SmartFares deal was found by Cheapflights users on 7/13. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:27 pm
ORD
-
BOS
1 stop5h 32m
JetBlue
Fri 9/44:55 pm
BOS
-
ORD
1 stop6h 03m
JetBlue
Deal found 7/13$176
This Traveloka deal was found by Cheapflights users on 7/13. 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 Traveloka is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:27 pm
ORD
-
BOS
1 stop5h 32m
JetBlue
Tue 8/1812:44 pm
BOS
-
ORD
1 stop5h 51m
JetBlue
Deal found 7/13$181
This Super.com deal was found by Cheapflights users on 7/13. 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.
Tue 9/226:30 am
ORD
-
BOS
1 stop7h 10m
JetBlue
Fri 9/254:00 pm
BOS
-
ORD
1 stop7h 06m
JetBlue
Deal found 7/13$182
This SmartFares deal was found by Cheapflights users on 7/12. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
ORD
-
BOS
1 stop7h 22m
JetBlue
Wed 9/212:57 pm
BOS
-
ORD
1 stop5h 38m
JetBlue
Deal found 7/12$183
This Jetabroad deal was found by Cheapflights users on 7/11. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:20 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Mon 8/175:21 pm
BOS
-
ORD
Nonstop3h 06m
JetBlue
Deal found 7/11$188
This Super.com deal was found by Cheapflights users on 7/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
-
BOS
1 stop6h 49m
JetBlue
Tue 8/182:45 pm
BOS
-
ORD
1 stop8h 13m
JetBlue
Deal found 7/15$193
This Super.com deal was found by Cheapflights users on 7/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:00 pm
ORD
-
BOS
1 stop6h 49m
JetBlue
Sun 9/203:13 pm
BOS
-
ORD
1 stop7h 53m
JetBlue
Deal found 7/16$194
This Cheapflightsfares deal was found by Cheapflights users on 7/11. 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.
Tue 9/1511:25 am
MKE
-
BOS
Nonstop2h 39m
JetBlue
Sat 9/198:45 am
BOS
-
MKE
Nonstop2h 50m
JetBlue
Deal found 7/11$195
This Delta deal was found by Cheapflights users on 7/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:35 pm
MKE
-
BOS
Nonstop2h 31m
Delta
Wed 9/169:15 am
BOS
-
MKE
Nonstop2h 40m
Delta
Deal found 7/14$197
This Super.com deal was found by Cheapflights users on 7/14. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:36 am
MKE
-
BOS
Nonstop2h 13m
JetBlue
Wed 9/27:10 am
BOS
-
MKE
Nonstop2h 34m
JetBlue
Deal found 7/14$205
This Delta deal was found by Cheapflights users on 7/13. 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.
Tue 9/156:35 pm
MKE
-
BOS
Nonstop2h 31m
Delta
Sat 9/195:40 am
BOS
-
MKE
1 stop4h 12m
Delta
Deal found 7/13$207
This CheapOair deal was found by Cheapflights users on 7/12. 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.
Tue 8/118:43 am
MKE
-
BOS
1 stop23h 26m
Multiple Airlines
Tue 8/187:10 am
BOS
-
MKE
Nonstop2h 34m
Multiple Airlines
Deal found 7/12$214

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 July 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$176
(SmartFares)

One-way from

$88
(SmartFares)

Popular in

February

Cheapest in

May

Average price

$302

Good round-trip deal

$217 or less

Good one-way deal

$132 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. 16% potential increase in price ($64 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 July 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 July 16, 2026.
Use the filters below to find and compare flights from Wisconsin to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 9/1

9:35 am-7:38 pm

1 stop9h 03m

Boston Logan Intl

Wed 9/9

6:55 am-8:46 am

Nonstop2h 51m

$199

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/29

12:53 pm-4:29 pm

Nonstop2h 36m

Boston Logan Intl

Sat 8/1

7:19 am-9:17 am

Nonstop2h 58m

$215

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 8/26

7:50 am-4:00 pm

1 stop7h 10m

Boston Logan Intl

Sat 8/29

5:50 am-12:40 pm

2 stops7h 50m

$222

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Tue 9/15

3:10 pm-10:15 pm

2 stops6h 05m

Boston Logan Intl

Sat 9/19

7:05 am-11:05 am

1 stop5h 00m

$222

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/28

9:40 pm-1:11 am

Nonstop2h 31m

Boston Logan Intl

Sun 8/30

5:45 am-9:38 am

1 stop4h 53m

$225

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 7/25

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

Tue 7/28

7:27 pm-11:31 pm

1 stop5h 04m

$225

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/15

3:37 pm-7:21 pm

Nonstop2h 44m

Boston Logan Intl

Sun 8/16

5:45 am-9:38 am

1 stop4h 53m

$225

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 9/16

4:57 pm-11:58 pm

1 stop6h 01m

Boston Logan Intl

Wed 9/23

7:00 am-12:43 pm

1 stop6h 43m

$227

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/16

1:00 pm-8:49 pm

1 stop6h 49m

Boston Logan Intl

Sat 9/19

6:55 am-11:47 am

1 stop5h 52m

$229

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 10/7

3:05 pm-6:44 pm

Nonstop2h 39m

Boston Logan Intl

Sun 10/11

7:30 am-9:24 am

Nonstop2h 54m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/11

Showing 1-10 of 60 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $65). Flying from Wisconsin to Boston in March is currently the most expensive (average of $197). 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 July 16, 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 38% on your trip compared to booking a flight at noon.

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

How far ahead should I book a flight from Wisconsin to Boston?

The price you pay for your flight from Wisconsin to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 82 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 July 11, 2026.

Travelers seeking maximum savings on their Wisconsin to Boston flight should consider departing on Tuesday at noon 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.

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 $215, JetBlue 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 Southwest, with whom users have recently found tickets for as low as $88. However, be on the lookout for offers from JetBlue 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 JetBlue (90%), Scandinavian Airlines (79%) or KLM (77%) 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 $255 for a flight from Wisconsin to Boston. The cheapest flight overall is $108 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $176.

  • 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, April is the cheapest month in which you can book a flight from Wisconsin to Boston (average of $65). Flying from Wisconsin to Boston in March is currently the most expensive (average of $197). 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
Waltham
Randolph
Cambridge
Concord
Brockton
Seekonk
Hampton Beach
Cranston
Dedham
Warwick
Peabody
Auburn
York Beach
Chelsea
Londonderry
Swansea
Fitchburg
North Falmouth
Braintree
Sandwich

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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 July 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$104Average$248FlexibilityNo cancel feeOn-time62%
DeltaCheapest$108Average$368FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$168Average$378FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$176Average$405FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$181Average$307FlexibilityNo cancel feeOn-time63%

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