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$165+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MSN
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Madison Truax Field are usually found in January or September, booked 83 days in advance, depart on a Tuesday or Thursday and return on a Monday

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 July 28, 2026.

This American Airlines deal was found by Cheapflights users on 7/27. 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 9/55:30 pm
BOS
-
MSN
Nonstop2h 55m
American Airlines
Tue 9/87:00 am
MSN
-
BOS
Nonstop2h 37m
American Airlines
Deal found 7/27$322
This Delta deal was found by Cheapflights users on 7/27. 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.
Wed 8/261:10 pm
BOS
-
MSN
Nonstop2h 55m
Delta
Sat 9/52:35 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Deal found 7/27$323
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:45 pm
BOS
-
MSN
2 stops20h 40m
Multiple Airlines
Sat 9/57:55 pm
MSN
-
BOS
1 stop12h 14m
Multiple Airlines
Deal found 7/27$325
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 10/287:43 pm
BOS
-
MSN
1 stop4h 42m
American Airlines
Tue 1/59:53 am
MSN
-
BOS
1 stop4h 56m
American Airlines
Deal found 7/27$342
This Delta deal was found by Cheapflights users on 7/27. 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.
Wed 8/265:30 am
BOS
-
MSN
1 stop5h 57m
Delta
Wed 9/25:15 pm
MSN
-
BOS
1 stop7h 10m
Delta
Deal found 7/27$343
This United Airlines deal was found by Cheapflights users on 7/23. 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.
Wed 8/268:05 am
BOS
-
MSN
1 stop4h 53m
United Airlines
Sat 8/294:01 pm
MSN
-
BOS
2 stops6h 58m
United Airlines
Deal found 7/23$348
This Delta deal was found by Cheapflights users on 7/27. 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 9/221:07 pm
BOS
-
MSN
Nonstop2h 48m
Delta
Mon 9/283:15 pm
MSN
-
BOS
Nonstop2h 39m
Delta
Deal found 7/27$357
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Sat 9/55:30 pm
BOS
-
MSN
Nonstop2h 55m
American Airlines
Mon 9/76:00 am
MSN
-
BOS
1 stop5h 14m
American Airlines
Deal found 7/26$367
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Wed 8/268:00 pm
BOS
-
MSN
Nonstop2h 46m
American Airlines
Sat 8/298:00 am
MSN
-
BOS
Nonstop2h 32m
American Airlines
Deal found 7/26$376

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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$322
(American Airlines)

One-way from

$165
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$471

Good round-trip deal

$381 or less

Good one-way deal

$318 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. 13% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 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 Boston Logan Intl to Madison Truax Field.
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 July 28, 2026.
Use the filters below to find and compare flights from Boston to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 8/22

5:51 am-11:26 am

1 stop6h 35m

Madison Truax Field

Tue 8/25

3:45 pm-7:19 pm

Nonstop2h 34m

$333

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Tue 8/25

7:05 am-11:58 am

1 stop5h 53m

Madison Truax Field

Tue 9/1

8:10 am-2:07 pm

1 stop4h 57m

$343

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 8/22

5:51 am-11:26 am

1 stop6h 35m

Madison Truax Field

Mon 8/24

3:45 pm-7:19 pm

Nonstop2h 34m

$401

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 9/5

3:00 pm-9:29 pm

1 stop7h 29m

Madison Truax Field

Mon 9/7

5:15 pm-1:25 am

1 stop7h 10m

$426
Quickest round-trip

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Thu 8/20

2:35 pm-4:25 pm

Nonstop2h 50m

Madison Truax Field

Mon 8/24

3:45 pm-7:19 pm

Nonstop2h 34m

$440

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 9/5

7:30 am-2:59 pm

2 stops8h 29m

Madison Truax Field

Mon 9/7

6:30 am-12:50 pm

1 stop5h 20m

$462

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 8/22

7:05 am-11:58 am

1 stop5h 53m

Madison Truax Field

Tue 8/25

2:47 pm-11:59 pm

2 stops8h 12m

$462

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Fri 8/21

3:14 pm-10:38 pm

1 stop8h 24m

Madison Truax Field

Fri 8/28

7:00 am-3:29 pm

1 stop7h 29m

$462
Cheapest one-way

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Tue 8/11

7:30 am-1:42 pm

2 stops7h 12m

$240
Quickest one-way

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Tue 10/27

1:07 pm-2:57 pm

Nonstop2h 50m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 17 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Madison flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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?

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 81 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, January is the cheapest month in which you can book a flight from Boston to Madison (average of $278). Flying from Boston to Madison in June is currently the most expensive (average of $510). 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 July 28, 2026.

A simple way to save on the total cost of your ticket is to fly from Boston to Madison in the afternoon. If you’re flexible enough to do this you can expect to save up to 15% on your trip compared to booking a flight in the morning.

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

Airfare is below average for this route at the moment.

Boston to Madison flights typically cost between $376 and $618 in September.
The cheapest round-trip price found within the last 5 days was $322 on American Airlines (Sep 5-Sep 8).

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 July 28, 2026.
Read through reviews of airlines operating flights from Boston to Madison, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,482 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.
Delta
7.8
Good
8,482 reviews
Delta
7.8
Good
8,482 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.
United Airlines
7.4
Good
10,046 reviews
Delta
7.8
Good
8,482 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.
American Airlines
7.1
Good
11,839 reviews
Delta
7.8
Good
8,482 reviews

Comfort

7.8

Food

7.2

Crew

8.5

Boarding

8.1

Entertainment

7.8

Overall

7.8

Reviews

1 / 20
10.0
Excellent

Stephanie,Sep 2023

LGA - MSN

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

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.

  • What airports do I use to fly from Boston to Madison?

    Booking a flight from Boston Logan Intl (BOS) to Madison Truax Field (MSN) is your only option if you wish to fly from Boston to Madison. On a typical day, there are 2 flights from Logan Intl to Truax Field, all of which are around 2h 45m for a nonstop flight. You can also purchase a plane ticket from 3 airlines when you book a flight from Logan Intl to Madison.

  • How popular is this Boston to Madison flight route?

    The Boston Logan Intl to Madison Truax Field flight path was viewed by 3 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

  • How long is the flight from Boston to Madison?

    Airlines like Delta and United Airlines fly from Boston to Madison in about 5h 53m. The time it takes to get you to your destination can typically vary by up to 42m. 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, American Airlines ($254), United Airlines ($258), and Delta ($258) offers the cheapest pricing from Boston to Madison. American Airlines is priced at 38% 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 United Airlines and Delta, with prices starting from $131 and $138, respectively.

  • What are the most reliable airlines from Boston to Madison?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Boston to Madison on time: Delta (90%), Republic Airways (78%), American Airlines (67%).

  • What are the cheapest flights from Boston to Madison?

    On average you can expect to pay $400 for a flight from Boston to Madison. The cheapest flight overall is $261 while the most popular route, (Boston Logan Intl - Madison Truax Field) is currently priced at $323.

  • 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, January is the cheapest month in which you can book a flight from Boston to Madison (average of $278). Flying from Boston to Madison in June is currently the most expensive (average of $510). 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
Sun Prairie
Middleton
Baraboo
Fitchburg

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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 July 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$254Average$408FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$258Average$443FlexibilityNo cancel feeOn-time69%
DeltaCheapest$258Average$460FlexibilityNo cancel feeOn-timeN/A

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