HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$164+ Cheap flights from Boston to Madison (BOS - MSN)

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 1/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MSN
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Boston to Madison 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.

Cheap flight deals from Boston to Madison

Cheapest flights from Boston to Madison
Explore the most affordable flight options available from Boston to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This American Airlines deal was found by Cheapflights users on 12/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:14 pmBOS - MSN
1 stop6h 31mAmerican Airlines
Thu 1/16:18 pmMSN - BOS
1 stop4h 33mAmerican Airlines
Deal found 12/13$317
This American Airlines deal was found by Cheapflights users on 12/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/142:44 pmBOS - MSN
1 stop5h 54mAmerican Airlines
Tue 1/64:30 pmMSN - BOS
1 stop6h 21mAmerican Airlines
Deal found 12/14$349
This American Airlines deal was found by Cheapflights users on 12/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/216:30 pmBOS - MSN
1 stop6h 29mAmerican Airlines
Thu 12/251:12 pmMSN - BOS
1 stop4h 20mAmerican Airlines
Deal found 12/13$388
This American Airlines deal was found by Cheapflights users on 12/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:53 amBOS - MSN
1 stop5h 12mAmerican Airlines
Mon 12/225:01 pmMSN - BOS
1 stop4h 54mAmerican Airlines
Deal found 12/12$399
This United Airlines deal was found by Cheapflights users on 12/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:40 pmBOS - MSN
2 stops9h 50mUnited Airlines
Thu 1/15:26 pmMSN - BOS
1 stop6h 19mUnited Airlines
Deal found 12/13$404
This American Airlines deal was found by Cheapflights users on 12/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:53 amBOS - MSN
1 stop5h 12mAmerican Airlines
Sun 12/2111:23 amMSN - BOS
1 stop9h 10mAmerican Airlines
Deal found 12/12$409
This United Airlines deal was found by Cheapflights users on 12/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/264:31 pmBOS - MSN
1 stop7h 26mUnited Airlines
Wed 12/313:46 pmMSN - BOS
2 stops7h 08mUnited Airlines
Deal found 12/13$410
This United Airlines deal was found by Cheapflights users on 12/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:30 amBOS - MSN
1 stop5h 24mUnited Airlines
Sun 12/213:46 pmMSN - BOS
2 stops7h 08mUnited Airlines
Deal found 12/12$414
This Delta deal was found by Cheapflights users on 12/13. 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.
Sat 12/132:59 pmBOS - MSN
1 stop6h 59mDelta
Sun 12/146:00 amMSN - BOS
1 stop6h 50mDelta
Deal found 12/13$419
This United Airlines deal was found by Cheapflights users on 12/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:51 pmBOS - MSN
1 stop6h 32mUnited Airlines
Sun 12/143:59 pmMSN - BOS
2 stops6h 42mUnited Airlines
Deal found 12/13$424
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/227:45 amBOS - MSN
1 stop7h 09mUnited Airlines
Wed 12/312:29 pmMSN - BOS
2 stops8h 25mUnited Airlines
Deal found 12/14$428
This Delta deal was found by Cheapflights users on 12/14. 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.
Thu 12/257:00 amBOS - MSN
1 stop6h 27mDelta
Wed 12/319:45 amMSN - BOS
1 stop12h 29mDelta
Deal found 12/14$442

Find flight deals from Boston to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$251
(United Airlines)

One-way from

$160
(American Airlines)

Popular in

January

Cheapest in

August

Average price

$473

Good one-way deal

$919 or less
Provider with most accurate pricing for Boston Logan Intl-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Madison Truax Field flights.
Search Deals
From Boston Logan Intl to Madison Truax Field
Search Deals
One-way flight from Boston Logan Intl to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Madison Truax Field.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Madison 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 December 15, 2025.
Use the filters below to find and compare flights from Boston to Madison that are best for you.

Fly from

Boston

Fly to

Madison

Route

Depart

Return

Price

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Fri 2/6

9:30 am-2:52 pm

1 stop6h 22m

Madison Truax Field

Mon 2/9

6:30 am-12:46 pm

1 stop5h 16m

$349

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Thu 1/22

6:00 am-11:51 am

1 stop6h 51m

Madison Truax Field

Thu 1/29

6:30 am-2:17 pm

2 stops6h 47m

$354

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Thu 1/22

7:25 am-2:38 pm

1 stop8h 13m

Madison Truax Field

Sun 1/25

6:30 am-5:14 pm

2 stops9h 44m

$354

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Fri 1/30

9:30 am-9:20 pm

2 stops12h 50m

Madison Truax Field

Sun 2/1

2:56 pm-11:49 pm

2 stops7h 53m

$359

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Thu 5/21

7:00 am-12:40 pm

1 stop6h 40m

Madison Truax Field

Sun 5/24

6:16 am-11:31 am

1 stop4h 15m

$397

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 1/3

5:45 am-10:10 am

1 stop5h 25m

$164

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Fri 2/27

7:11 pm-11:28 pm

1 stop5h 17m

$164

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Tue 4/28

6:33 pm-10:40 pm

1 stop5h 07m

$164

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Tue 3/10

3:15 pm-10:56 pm

1 stop8h 41m

$164

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Mon 3/9

7:16 pm-11:25 pm

1 stop5h 09m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 13 results
1
2

Compare providers for flights from Boston to Madison

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Madison in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Boston-Madison flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Boston-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Madison flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Boston to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Boston 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 Boston to Madison

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

Use this chart to determine the optimal time to book a round-trip flight from Boston to Madison. Price data was last updated on December 12, 2025.

The price you pay for your flight from Boston to Madison may vary depending on when you book. For the best chance of a lower fare, look to book 88 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 Boston to Madison?

Currently, September is the cheapest month in which you can book a flight from Boston to Madison (average of $98). Flying from Boston to Madison in February is currently the most expensive (average of $258). 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 BOS to MSN?

Find hourly flight availability from Boston to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

A simple way to save on the total cost of your ticket is to fly from Boston to Madison in the morning. If you’re flexible enough to do this you can expect to save up to 61% on your trip compared to booking a flight in the evening.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated December 15, 2025.
Read through reviews of airlines operating flights from Boston to Madison, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,008 reviews

Overall

7.9

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,092 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,052 reviews
Delta
7.9
Good
8,008 reviews

Overall

7.9

Entertainment

7.9

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Boston to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Boston to Madison?

    Airlines like United Airlines and American Airlines fly from Boston to Madison in about 5h 27m. The time it takes to get you to your destination can typically vary by up to 35m. The distance from Boston to Madison is about 929 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Boston to Madison round-trip?

    According to our current data, Delta ($250), American Airlines ($254), and United Airlines ($306) offers the cheapest pricing from Boston to Madison. Delta is priced at 41% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Boston to Madison one-way?

    $125 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $129 and $138, respectively.

  • What are the cheapest flights from Boston to Madison?

    On average you can expect to pay $1,566 for a flight from Boston to Madison. The cheapest flight overall is $919 while the most popular route, (Boston Logan Intl - Madison Truax Field) is currently priced at $251.

  • Can I find deals for flights from Boston to Madison that include hotel bookings?

    Yes. In addition to deals on Boston to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Madison.

  • Can I find deals for business class flights from Boston to Madison?

    Yes. Cheapflights offers flight deals from Boston to Madison 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 Boston to Madison?

    Currently, September is the cheapest month in which you can book a flight from Boston to Madison (average of $98). Flying from Boston to Madison in February is currently the most expensive (average of $258). 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 Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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 Boston to Madison

See prices for flight routes from nearby airports that may be better suited for you.
Boston to O'Hare Intl flights
Hartford to O'Hare Intl flights
Boston to Minneapolis flights
Boston to Milwaukee flights
Albany to O'Hare Intl flights
Hartford to Minneapolis flights
Hartford to Milwaukee flights
Albany to Minneapolis flights
Hartford to Appleton flights
Boston to Appleton flights
Albany to Milwaukee flights
Boston to Green Bay flights
Albany to Madison flights
Hartford to Madison flights
Boston to Duluth flights
Hyannis to O'Hare Intl flights
Hartford to Green Bay flights
Worcester to O'Hare Intl flights
West Tisbury to O'Hare Intl flights
Albany to Green Bay flights
Albany to Wausau flights
Nantucket to O'Hare Intl flights
Hartford to Duluth flights
Boston to La Crosse flights
West Tisbury to Minneapolis flights
Provincetown to O'Hare Intl flights
New Bedford to O'Hare Intl flights
Boston to Wausau flights
Hyannis to Minneapolis flights
Boston to Escanaba flights
Boston to Dubuque flights
Hartford to La Crosse flights

Top 3 airlines flying from Boston to Madison

Discover the top 3 airlines that operate flights from Boston to Madison. 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$250Average$415FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$368FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$306Average$428FlexibilityNo 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.