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$84+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
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 May 11, 2026.

This Delta deal was found by Cheapflights users on 5/6. 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 5/307:00 am
ORD
-
BOS
Nonstop2h 35m
Delta
Sat 5/305:30 pm
BOS
-
ORD
Nonstop3h 03m
Delta
Deal found 5/6$167
This SmartFares deal was found by Cheapflights users on 5/10. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:56 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Sun 5/316:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/10$168
This Cheapflightsfares deal was found by Cheapflights users on 5/6. 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.
Sat 5/301:56 pm
ORD
-
BOS
Nonstop2h 31m
JetBlue
Tue 6/26:00 am
BOS
-
ORD
Nonstop3h 00m
JetBlue
Deal found 5/6$172
This United Airlines deal was found by Cheapflights users on 5/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:45 pm
ORD
-
BOS
Nonstop2h 36m
United Airlines
Tue 6/25:05 pm
BOS
-
ORD
Nonstop3h 00m
United Airlines
Deal found 5/8$177
This Cheapflightsfares deal was found by Cheapflights users on 5/6. 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 5/278:30 pm
ORD
-
BOS
Nonstop2h 29m
JetBlue
Sat 6/611:00 am
BOS
-
ORD
Nonstop2h 59m
JetBlue
Deal found 5/6$181
This Cheapflightsfares deal was found by Cheapflights users on 5/6. 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 5/298:50 am
ORD
-
BOS
Nonstop2h 30m
JetBlue
Mon 6/158:10 am
BOS
-
ORD
Nonstop2h 56m
JetBlue
Deal found 5/6$186
This Delta deal was found by Cheapflights users on 5/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/234:30 pm
ORD
-
BOS
Nonstop2h 36m
Delta
Tue 5/267:35 am
BOS
-
ORD
Nonstop2h 52m
Delta
Deal found 5/8$187
This American Airlines deal was found by Cheapflights users on 5/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:17 pm
MKE
-
BOS
1 stop5h 20m
American Airlines
Tue 7/147:27 pm
BOS
-
MKE
1 stop5h 25m
American Airlines
Deal found 5/10$187
This American Airlines deal was found by Cheapflights users on 5/9. 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.
Sat 5/305:20 pm
ORD
-
BOS
Nonstop2h 33m
American Airlines
Sun 5/317:00 am
BOS
-
ORD
Nonstop3h 04m
American Airlines
Deal found 5/9$188
This Frontier deal was found by Cheapflights users on 5/6. 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.
Wed 6/312:09 pm
MKE
-
BOS
1 stop12h 15m
Frontier
Wed 6/106:00 am
BOS
-
MKE
1 stop6h 13m
Frontier
Deal found 5/6$190
This Priceline deal was found by Cheapflights users on 5/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:41 am
MKE
-
BOS
Nonstop2h 19m
Multiple Airlines
Wed 6/36:00 am
BOS
-
MKE
1 stop6h 14m
Multiple Airlines
Deal found 5/10$199
This Cheapflightsfares deal was found by Cheapflights users on 5/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:41 am
MKE
-
BOS
Nonstop2h 19m
JetBlue
Wed 6/106:15 am
BOS
-
MKE
Nonstop2h 36m
JetBlue
Deal found 5/10$202

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 May 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$167
(flygcity.se)

One-way from

$84
(United Airlines)

Popular in

February

Cheapest in

September

Average price

$279

Good round-trip deal

$198 or less

Good one-way deal

$128 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. 15% potential increase in price ($62 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 May 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 May 11, 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

Sat 5/30

1:56 pm-5:27 pm

Nonstop2h 31m

Boston Logan Intl

Sun 5/31

6:00 am-8:00 am

Nonstop3h 00m

$182
Quickest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/20

7:00 am-10:35 am

Nonstop2h 35m

Boston Logan Intl

Mon 5/25

12:55 pm-2:48 pm

Nonstop2h 53m

$192

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/30

7:45 pm-11:21 pm

Nonstop2h 36m

Boston Logan Intl

Mon 6/1

7:00 pm-11:30 pm

1 stop5h 30m

$202

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Wed 7/1

7:23 pm-1:14 am

1 stop4h 51m

Boston Logan Intl

Tue 7/7

6:00 am-9:53 am

1 stop4h 53m

$205

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/15

12:53 pm-4:29 pm

Nonstop2h 36m

Boston Logan Intl

Tue 7/21

5:45 am-9:36 am

1 stop4h 51m

$207

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/30

6:00 am-11:16 am

1 stop4h 16m

Boston Logan Intl

Wed 7/8

6:43 pm-8:40 pm

Nonstop2h 57m

$221

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/28

2:40 pm-11:55 pm

2 stops8h 15m

Boston Logan Intl

Mon 6/1

5:30 am-12:50 pm

2 stops8h 20m

$227

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/22

9:41 pm-1:14 am

Nonstop2h 33m

Boston Logan Intl

Mon 5/25

6:00 am-7:58 am

Nonstop2h 58m

$227

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 7/18

4:59 pm-11:59 pm

1 stop6h 00m

Boston Logan Intl

Sat 7/25

11:40 am-1:15 pm

Nonstop2h 35m

$237

MilwaukeeBoston

MKE - BOS

MKEBOS

Milwaukee-Mitchell

Sat 7/18

4:40 pm-12:15 am

1 stop6h 35m

Boston Logan Intl

Sat 7/25

5:10 am-9:25 am

1 stop5h 15m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

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

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 62 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 $78). 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 May 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 78% 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 May 2, 2026.

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

Weekly flight availability from Wisconsin to Boston

Explore weekly flight availability from Wisconsin to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 11, 2026.

The most flights from USWI to BOS are scheduled on a Tuesday (9 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 on average).

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 $182, JetBlue can have you in Boston from Wisconsin in 2h 31m. 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 $78. However, be on the lookout for offers from Southwest 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 (93%), Delta (93%) or Republic Airways (93%) 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 $240 for a flight from Wisconsin to Boston. The cheapest flight overall is $93 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $177.

  • 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 $78). 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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Chelsea
Peabody
Seabrook
York Beach
Warwick
Londonderry
Cranston
Swansea
Old Orchard Beach
Auburn
Quincy
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 May 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$88Average$241FlexibilityNo cancel feeOn-time62%
DeltaCheapest$103Average$366FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$258FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$377FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$192Average$386FlexibilityNo cancel feeOn-time69%

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