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$126+ Cheap flights from Madison (MSN) to Massachusetts

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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — BOS
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheap flight deals from Madison to Massachusetts

Keep the following information in mind while searching for Madison to Massachusetts flight deals. Data was last updated September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(Delta)

One-way from

$126
(Delta)

Popular in

February

Cheapest in

August

Average price

$330
Provider with most accurate pricing for Madison Truax Field-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Boston Logan Intl flights.
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From Madison Truax Field to Massachusetts
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One-way flight from Madison Truax Field to Massachusetts
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Highest demand for flights based on searches. 14% potential increase in price ($74 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Madison to Massachusetts

Cheapest flights from Madison to Massachusetts
Explore the most affordable flight options available from Madison to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/55:11 pmMSN - ALB
1 stop5h 46mDelta
Wed 11/121:50 pmALB - MSN
1 stop7h 24mDelta
Deal found 9/29$249
This Delta deal was found by Cheapflights users on 9/27. 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.
Thu 10/305:11 pmMSN - BDL
1 stop5h 18mDelta
Sun 11/25:10 amBDL - MSN
1 stop5h 08mDelta
Deal found 9/27$249
This American Airlines deal was found by Cheapflights users on 9/27. 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 11/199:48 amMSN - BOS
1 stop4h 15mAmerican Airlines
Sat 11/226:15 pmBOS - MSN
1 stop6h 36mAmerican Airlines
Deal found 9/27$251
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/155:15 pmMSN - ALB
1 stop5h 42mDelta
Tue 10/216:03 amALB - MSN
1 stop5h 29mDelta
Deal found 9/29$254
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/175:15 pmMSN - BDL
1 stop5h 14mDelta
Tue 10/214:56 pmBDL - MSN
1 stop6h 49mDelta
Deal found 9/29$254
This Delta deal was found by Cheapflights users on 9/27. 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 11/195:30 pmMSN - BOS
1 stop5h 17mDelta
Sun 11/235:50 amBOS - MSN
1 stop7h 53mDelta
Deal found 9/27$255
This United Airlines deal was found by Cheapflights users on 9/28. 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 12/32:48 pmMSN - BDL
2 stops8h 11mUnited Airlines
Sat 12/66:00 amBDL - MSN
2 stops9h 01mUnited Airlines
Deal found 9/28$259
This Delta deal was found by Cheapflights users on 9/28. 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 11/136:00 amMSN - BOS
1 stop6h 54mDelta
Sun 11/168:00 amBOS - MSN
1 stop5h 43mDelta
Deal found 9/28$259
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Fri 10/177:40 amMSN - BOS
1 stop7h 18mAmerican Airlines
Tue 10/216:00 amBOS - MSN
1 stop7h 15mAmerican Airlines
Deal found 9/27$270
This American Airlines deal was found by Cheapflights users on 9/27. 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.
Thu 12/187:00 amMSN - BOS
1 stop6h 14mAmerican Airlines
Sun 1/115:47 amBOS - MSN
1 stop5h 42mAmerican Airlines
Deal found 9/27$274
This United Airlines deal was found by Cheapflights users on 9/28. 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 10/86:30 amMSN - BDL
1 stop7h 03mUnited Airlines
Sun 10/126:00 amBDL - MSN
1 stop4h 55mUnited Airlines
Deal found 9/28$284
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/75:52 pmMSN - BOS
1 stop5h 07mDelta
Wed 10/2210:30 amBOS - MSN
1 stop4h 55mDelta
Deal found 9/29$284

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Massachusetts 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 September 29, 2025.
Use the filters below to find and compare flights from Madison to Massachusetts that are best for you.

Fly from

Madison

Fly to

Massachusetts

Route

Depart

Return

Price

MadisonAlbany

MSN - ALB

MSNALB

Madison Truax Field

Wed 11/5

5:21 pm-11:16 pm

1 stop4h 55m

Albany Intl

Wed 11/12

6:00 am-8:52 am

1 stop3h 52m

$249

MadisonHartford

MSN - BDL

MSNBDL

Madison Truax Field

Sat 10/18

4:15 pm-11:01 pm

1 stop5h 46m

Hartford Bradley Intl

Sat 10/25

6:30 am-12:04 pm

1 stop6h 34m

$249

MadisonHartford

MSN - BDL

MSNBDL

Madison Truax Field

Wed 2/18

5:50 pm-11:39 pm

1 stop4h 49m

Hartford Bradley Intl

Sat 2/21

5:00 pm-8:48 pm

1 stop4h 48m

$249

MadisonHartford

MSN - BDL

MSNBDL

Madison Truax Field

Sat 10/18

5:22 pm-11:30 pm

1 stop5h 08m

Hartford Bradley Intl

Sat 10/25

6:10 am-10:18 am

1 stop5h 08m

$249

MadisonHartford

MSN - BDL

MSNBDL

Madison Truax Field

Tue 10/28

5:52 pm-11:29 pm

1 stop4h 37m

Hartford Bradley Intl

Sun 11/2

5:10 am-9:18 am

1 stop5h 08m

$249

MadisonHartford

MSN - BDL

MSNBDL

Madison Truax Field

Sat 11/8

5:33 pm-11:14 pm

1 stop4h 41m

Hartford Bradley Intl

Sun 11/9

6:05 am-12:43 pm

1 stop7h 38m

$249

MadisonHartford

MSN - BDL

MSNBDL

Madison Truax Field

Fri 10/31

2:42 pm-11:29 pm

1 stop7h 47m

Hartford Bradley Intl

Sun 11/2

5:10 am-9:18 am

1 stop5h 08m

$249

MadisonHartford

MSN - BDL

MSNBDL

Madison Truax Field

Wed 12/31

5:03 pm-11:13 pm

1 stop5h 10m

Hartford Bradley Intl

Sat 1/3

5:20 am-9:05 am

1 stop4h 45m

$249

MadisonHartford

MSN - BDL

MSNBDL

Madison Truax Field

Wed 12/3

6:18 pm-11:38 pm

1 stop4h 20m

Hartford Bradley Intl

Sat 12/6

6:09 am-10:15 am

1 stop5h 06m

$249

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 12/6

9:40 am-4:03 pm

1 stop5h 23m

Boston Logan Intl

Tue 12/9

10:00 am-2:35 pm

1 stop5h 35m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/27

Showing 1-10 of 53 results
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Best time to book a flight from Madison to Massachusetts

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

What is the cheapest month to book a flight from Madison to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Madison to Massachusetts (average of $218). Flying from Madison to Massachusetts in July is currently the most expensive (average of $311). 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 MSN to MA?

Find hourly flight availability from Madison to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 29, 2025.

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

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated September 29, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Madison to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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
8,924 reviews
Delta
8.0
Very good
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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
7,964 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

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 Madison to Massachusetts. 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 from for flights from Madison to Massachusetts?

    Madison Truax Field (MSN), located 5.4 mi from the city center, is the airport you fly out of when you book flights from Madison to Massachusetts.

  • How long is the flight from Madison to Massachusetts?

    Delta and American Airlines can get you from Madison to Massachusetts in just under 4h 55m. Your travel time can differ by up to 15h 57m. The distance from Madison to Massachusetts is about 784 mi. This flight may include one or multiple stops.

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

    One-way options have recently been found by users for as low as $126 on Delta. Other airlines that offer cheap prices include American Airlines from $126 and United Airlines from $130 one-way.

  • What are the most popular routes from Madison to Massachusetts?

    Most travelers choose Madison Truax Field - Boston Logan Intl, Madison Truax Field - Hartford Bradley Intl or Madison Truax Field - Albany Intl when deciding on the best route from Madison to Massachusetts.

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

    No one likes to see their flight delayed. When booking a flight from Madison to Massachusetts consider choosing KLM (100%), Delta (100%) or American Airlines (0%) as they are the most reliable in getting you off to your destination on time.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Madison to Massachusetts (average of $218). Flying from Madison to Massachusetts in July is currently the most expensive (average of $311). 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

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Alternative routes for Madison to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Madison to Massachusetts

Discover the top 3 airlines that operate flights from Madison to Massachusetts. 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$250Average$489FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$252Average$385FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$266Average$456FlexibilityNo cancel feeOn-time69%

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