HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — BOS
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Boston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 26, 2025.

This American Airlines deal was found by Cheapflights users on 11/26. 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.
Mon 12/155:12 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Thu 1/16:36 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Deal found 11/26$122
This Trip.com deal was found by Cheapflights users on 11/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:38 pmORD - BOS
Nonstop2h 28mJetBlue
Sun 12/75:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Deal found 11/24$124
This United Airlines deal was found by Cheapflights users on 11/24. 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 12/56:17 pmORD - BOS
Nonstop2h 28mUnited Airlines
Wed 12/109:40 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 11/24$127
This Trip.com deal was found by Cheapflights users on 11/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/411:25 amORD - BOS
Nonstop2h 24mJetBlue
Sun 12/78:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/24$128
This Trip.com deal was found by Cheapflights users on 11/26. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/58:38 pmORD - BOS
Nonstop2h 28mJetBlue
Mon 12/88:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/26$129
This JetBlue deal was found by Cheapflights users on 11/26. 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 12/287:41 pmORD - BOS
Nonstop2h 29mJetBlue
Sat 1/35:00 pmBOS - ORD
Nonstop3h 20mJetBlue
Deal found 11/26$131
This American Airlines deal was found by Cheapflights users on 11/24. 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.
Tue 12/92:42 pmORD - BOS
Nonstop2h 29mAmerican Airlines
Sun 1/116:43 amBOS - ORD
Nonstop3h 14mAmerican Airlines
Deal found 11/24$132
This Delta deal was found by Cheapflights users on 11/24. 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.
Fri 12/197:10 amORD - BOS
Nonstop2h 26mDelta
Wed 1/71:50 pmBOS - ORD
Nonstop3h 07mDelta
Deal found 11/24$137
This United Airlines deal was found by Cheapflights users on 11/25. 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.
Mon 12/229:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Sat 1/179:30 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/25$138
This United Airlines deal was found by Cheapflights users on 11/25. 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.
Mon 12/229:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Wed 12/316:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/25$141
This JetBlue deal was found by Cheapflights users on 11/25. 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.
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Tue 12/168:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/25$142
This Cheapflightsfares deal was found by Cheapflights users on 11/25. 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 12/196:54 amMSP - BOS
Nonstop2h 57mSun Country Air
Thu 12/2510:19 amBOS - MSP
Nonstop3h 11mSun Country Air
Deal found 11/25$188

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 November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$59
(United Airlines)

Popular in

November

Cheapest in

May

Average price

$438

Good round-trip deal

$368 or less

Good one-way deal

$208 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. 11% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 26, 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

Fri 12/12

8:38 pm-12:06 am

Nonstop2h 28m

Boston Logan Intl

Tue 12/16

8:30 am-10:35 am

Nonstop3h 05m

$122

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/5

4:05 pm-7:25 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

6:00 am-8:00 am

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 1/12

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sat 1/17

5:15 pm-7:26 pm

Nonstop3h 11m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

8:38 pm-12:06 am

Nonstop2h 28m

Boston Logan Intl

Mon 12/8

8:30 am-10:35 am

Nonstop3h 05m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

Sun 12/7

9:40 am-11:40 am

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/15

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Sat 1/17

5:15 pm-7:26 pm

Nonstop3h 11m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/14

7:05 am-10:40 am

Nonstop2h 35m

Boston Logan Intl

Thu 1/22

11:30 am-1:39 pm

Nonstop3h 09m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/23

4:15 pm-7:39 pm

Nonstop2h 24m

Boston Logan Intl

Mon 1/26

4:16 pm-6:16 pm

Nonstop3h 00m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/13

11:00 am-2:28 pm

Nonstop2h 28m

Boston Logan Intl

Wed 1/21

8:25 pm-10:29 pm

Nonstop3h 04m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/7

5:00 pm-8:21 pm

Nonstop2h 21m

Boston Logan Intl

Mon 1/12

7:55 pm-10:01 pm

Nonstop3h 06m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/26

Showing 1-10 of 60 results
1
2
3
...
6

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 December is currently the most expensive (average of $246). 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 November 26, 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 44% 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 $127, JetBlue can have you in Boston from Wisconsin in 2h 20m. 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 Delta, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from United Airlines and JetBlue, 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 (58%), Virgin Atlantic (56%) or KLM (53%) 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 $938 for a flight from Wisconsin to Boston. The cheapest flight overall is $123 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $114.

  • 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 December is currently the most expensive (average of $246). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Boston

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to Boston flights
Dallas/Fort Worth to Boston flights
San Francisco to Boston flights
LaGuardia to Boston flights
Seattle to Boston flights
Baltimore to Boston flights
Reagan-National to Boston flights
O'Hare Intl to Boston flights
Dulles Intl to Boston flights
John F Kennedy Intl to Boston flights
Denver to Boston flights
Atlanta to Boston flights
Newark to Boston flights
Tampa to Boston flights
Orlando to Boston flights
Charlotte to Boston flights
Philadelphia to Boston flights
Hobby to Boston flights
Raleigh to Boston flights
Fort Lauderdale to Boston flights
George Bush Intcntl to Boston flights
Detroit to Boston flights
Austin to Hartford flights
Orlando to Hartford flights
Ontario to Boston flights
Miami to Boston flights
Sky Harbor Intl to Boston flights
Richmond to Boston flights
Midway to Boston flights
Austin to Boston flights
Cleveland to Boston flights
Nashville to Boston flights
Minneapolis to Boston flights
Portland to Boston flights
Salt Lake City to Boston flights
Indianapolis to Boston flights
Fort Myers to Boston flights
Cincinnati to Boston flights
Jacksonville to Boston flights
O'Hare Intl to Hartford flights
San Diego to Boston flights
Pittsburgh to Boston flights
Tampa to Hartford flights
West Palm Beach to Boston flights
Fort Lauderdale to Hartford flights
Love Field to Boston flights
Islip to Boston flights
Columbus to Boston flights
San Antonio to Boston flights
Las Vegas to Boston flights

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 November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$114Average$280FlexibilityNo cancel feeOn-time62%
DeltaCheapest$151Average$389FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$176Average$261FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$176Average$415FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$192Average$391FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.