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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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MSN
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$255
(American Airlines)

One-way from

$100
(American Airlines)

Popular in

January

Cheapest in

August

Average price

$387

Good round-trip deal

$576 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. 15% potential increase in price ($87 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip 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 July 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/29. 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 8/226:21 pmBOS - MSN
1 stop5h 42mAmerican Airlines
Tue 8/266:45 amMSN - BOS
1 stop7h 36mAmerican Airlines
Deal found 7/29$255
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/67:45 amBOS - MSN
1 stop4h 59mUnited Airlines
Wed 9/106:30 amMSN - BOS
2 stops6h 43mUnited Airlines
Deal found 7/27$256
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 8/135:15 amBOS - MSN
1 stop4h 29mDelta
Tue 8/196:00 amMSN - BOS
1 stop7h 14mDelta
Deal found 7/27$260

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 29, 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 8/22

6:21 pm-11:03 pm

1 stop5h 42m

Madison Truax Field

Tue 8/26

6:45 am-3:21 pm

1 stop7h 36m

$255

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 9/6

7:45 am-11:44 am

1 stop4h 59m

Madison Truax Field

Wed 9/10

6:30 am-2:13 pm

2 stops6h 43m

$256

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Wed 8/13

5:15 am-8:44 am

1 stop4h 29m

Madison Truax Field

Tue 8/19

6:00 am-2:14 pm

1 stop7h 14m

$260

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 8/30

5:28 am-9:18 am

1 stop4h 50m

$100

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 8/30

5:34 am-10:19 am

1 stop5h 45m

$119

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Sat 8/30

1:00 pm-10:23 pm

2 stops10h 23m

$140

BostonMadison

BOS - MSN

BOSMSN

Boston Logan Intl

Fri 8/22

6:05 am-8:01 am

2 stops26h 56m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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 July 25, 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 July 29, 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 July 29, 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
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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
8,899 reviews
Delta
8.0
Very good
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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
7,977 reviews

Food

7.3

Crew

8.5

Boarding

8.2

Overall

8.0

Entertainment

7.9

Comfort

7.9

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.

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

    According to our current data, American Airlines ($255), United Airlines ($256), and Delta ($260) offers the cheapest pricing from Boston to Madison. American Airlines is priced at 45% 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 Delta and United Airlines, with prices starting from $119 and $140, respectively.

  • What are the cheapest flights from Boston to Madison?

    On average you can expect to pay $663 for a flight from Boston to Madison. The cheapest flight overall is $576 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$414FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$486FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$303Average$549FlexibilityNo cancel feeOn-time69%

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