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$100+ 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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MSN
oct. 11 — oct. 181
sam. 10/11
sam. 10/18
1 adult, Economy
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Cheap 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 septembre 11, 2025.

Round-trip from

$255
(Delta)

One-way from

$100
(American Airlines)

Popular in

January

Cheapest in

August

Average price

$385

Good one-way deal

$919 or less
From Boston Logan Intl to Madison Truax Field
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One-way flight from Boston Logan Intl to Madison Truax Field
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Highest demand for flights based on searches. 16% potential increase in price ($88 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Boston Logan Intl to Madison Truax Field.
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Find 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 septembre 11, 2025.

This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/305:34 amBOS - MSN
1 stop4h 06mDelta
mar. 11/46:00 amMSN - BOS
1 stop6h 53mDelta
Deal found 9/10$255
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 10/226:00 amBOS - MSN
1 stop4h 55mUnited Airlines
mar. 10/282:48 pmMSN - BOS
2 stops7h 54mUnited Airlines
Deal found 9/9$256
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/26:00 amBOS - MSN
1 stop4h 55mUnited Airlines
dim. 10/56:11 amMSN - BOS
1 stop6h 14mUnited Airlines
Deal found 9/9$259
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 10/115:19 pmBOS - MSN
1 stop6h 44mUnited Airlines
mar. 10/146:17 amMSN - BOS
1 stop6h 08mUnited Airlines
Deal found 9/9$264
This American Airlines deal was found by Cheapflights users on 9/9. 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.
mer. 12/315:30 pmBOS - MSN
1 stop7h 07mAmerican Airlines
jeu. 1/14:05 pmMSN - BOS
1 stop5h 11mAmerican Airlines
Deal found 9/9$269
This American Airlines deal was found by Cheapflights users on 9/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 10/306:00 amBOS - MSN
1 stop7h 04mAmerican Airlines
dim. 11/25:50 amMSN - BOS
1 stop7h 48mAmerican Airlines
Deal found 9/11$274
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/315:31 amBOS - MSN
1 stop4h 34mDelta
mer. 12/315:03 pmMSN - BOS
1 stop5h 12mDelta
Deal found 9/9$277
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/295:31 amBOS - MSN
1 stop4h 34mDelta
ven. 1/25:03 pmMSN - BOS
1 stop5h 55mDelta
Deal found 9/9$279
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/204:23 pmBOS - MSN
1 stop7h 10mUnited Airlines
mer. 10/2210:51 amMSN - BOS
1 stop5h 11mUnited Airlines
Deal found 9/9$284
This Delta deal was found by Cheapflights users on 9/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/295:31 amBOS - MSN
1 stop4h 34mDelta
mer. 12/315:03 pmMSN - BOS
1 stop5h 12mDelta
Deal found 9/9$287
This American Airlines deal was found by Cheapflights users on 9/9. 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.
ven. 10/35:00 amBOS - MSN
1 stop5h 43mAmerican Airlines
dim. 10/55:00 amMSN - BOS
1 stop4h 29mAmerican Airlines
Deal found 9/9$288

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 septembre 11, 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

jeu. 10/30

5:34 am-8:40 am

1 stop4h 06m

Madison Truax Field

mar. 11/4

6:00 am-1:53 pm

1 stop6h 53m

$255

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

mer. 10/22

6:00 am-9:55 am

1 stop4h 55m

Madison Truax Field

mar. 10/28

2:48 pm-11:42 pm

2 stops7h 54m

$256

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

jeu. 1/8

10:00 am-3:04 pm

1 stop6h 04m

Madison Truax Field

dim. 1/11

3:52 pm-9:20 pm

1 stop4h 28m

$259

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

mar. 12/30

5:31 am-9:05 am

1 stop4h 34m

Madison Truax Field

sam. 1/3

10:50 am-7:41 pm

1 stop7h 51m

$259

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

jeu. 11/13

9:26 am-2:44 pm

1 stop6h 18m

Madison Truax Field

lun. 11/17

3:37 pm-10:20 pm

1 stop5h 43m

$259

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

ven. 12/19

6:01 am-11:48 am

1 stop6h 47m

Madison Truax Field

sam. 12/27

2:29 pm-9:44 pm

1 stop6h 15m

$259

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

jeu. 12/4

5:45 am-12:42 pm

1 stop7h 57m

Madison Truax Field

dim. 12/7

6:18 pm-11:54 pm

1 stop4h 36m

$259

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

jeu. 10/30

6:00 am-12:04 pm

1 stop7h 04m

Madison Truax Field

dim. 11/2

5:50 am-2:38 pm

1 stop7h 48m

$274

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

mar. 11/18

5:22 pm-10:49 pm

1 stop6h 27m

Madison Truax Field

jeu. 11/20

3:59 pm-10:22 pm

1 stop5h 23m

$274

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

ven. 9/26

8:00 am-2:27 pm

1 stop7h 27m

Madison Truax Field

lun. 9/29

5:26 pm-11:59 pm

1 stop5h 33m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 22 results
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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 August 29, 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 90 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 $338). Flying from Boston to Madison in March is currently the most expensive (average of $422). 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 septembre 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Boston to Madison as you normally would.

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 septembre 11, 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
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 Delta, United Airlines, and American Airlines fly from Boston to Madison in about 4h 06m. The time it takes to get you to your destination can typically vary by up to 1h 58m. 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 ($254), American Airlines ($254), and United Airlines ($307) offers the cheapest pricing from Boston to Madison. Delta is priced at 44% 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?

    $100 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 $126 and $126, 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: American Airlines (0%), KLM (0%), Envoy Air (0%).

  • 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 $158 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, January is the cheapest month in which you can book a flight from Boston to Madison (average of $338). Flying from Boston to Madison in March is currently the most expensive (average of $422). 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

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Alternative routes for Boston to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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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 septembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$254Average$482FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$254Average$416FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$307Average$541FlexibilityNo cancel feeOn-time69%

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