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$100+ Cheap flights from Madison to Boston (MSN - BOS)

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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — BOS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Boston Logan Intl are usually found in September or August, booked 43 days in advance, depart on a Wednesday or Monday and return on a Monday

Cheap flight deals from Madison to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Boston (BOS). 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 September 11, 2025.

Round-trip from

$255
(American Airlines)

One-way from

$100
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$336
From Madison Truax Field to Boston Logan Intl
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One-way flight from Madison Truax Field to Boston Logan Intl
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Highest demand for flights based on searches. 14% potential increase in price ($71 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 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 Boston

Cheapest flights from Madison to Boston
Explore the most affordable flight options available from Madison to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

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.
Sat 11/15:20 pmMSN - BOS
1 stop5h 29mDelta
Thu 11/65:34 amBOS - MSN
1 stop4h 06mDelta
Deal found 9/9$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.
Tue 9/303:48 pmMSN - BOS
2 stops7h 11mUnited Airlines
Sat 10/48:00 amBOS - MSN
1 stop4h 45mUnited Airlines
Deal found 9/9$256
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.
Fri 10/245:30 pmMSN - BOS
1 stop5h 19mDelta
Thu 10/305:34 amBOS - MSN
1 stop4h 06mDelta
Deal found 9/9$259
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/56:30 amMSN - BOS
1 stop5h 05mUnited Airlines
Sat 10/1112:34 pmBOS - MSN
2 stops7h 21mUnited Airlines
Deal found 9/10$260
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:17 amMSN - BOS
1 stop4h 36mUnited Airlines
Sat 10/115:19 pmBOS - MSN
1 stop6h 44mUnited Airlines
Deal found 9/11$264
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.
Wed 9/246:12 amMSN - BOS
1 stop7h 08mDelta
Tue 10/145:45 amBOS - MSN
1 stop6h 40mDelta
Deal found 9/10$270
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.
Wed 9/245:00 amMSN - BOS
1 stop5h 53mAmerican Airlines
Tue 10/145:24 amBOS - MSN
1 stop7h 03mAmerican 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.
Wed 10/81:19 pmMSN - BOS
1 stop5h 42mDelta
Tue 10/145:34 amBOS - MSN
1 stop4h 06mDelta
Deal found 9/9$275
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.
Tue 10/285:21 pmMSN - BOS
1 stop5h 28mDelta
Fri 10/3110:30 amBOS - MSN
1 stop4h 55mDelta
Deal found 9/9$279
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/205:45 pmMSN - BOS
1 stop6h 05mUnited Airlines
Wed 10/2211:02 amBOS - MSN
1 stop5h 04mUnited Airlines
Deal found 9/10$284
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.
Sat 10/410:51 amMSN - BOS
2 stops7h 05mUnited Airlines
Tue 10/76:15 pmBOS - MSN
1 stop5h 13mUnited Airlines
Deal found 9/9$288

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Boston 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 11, 2025.
Use the filters below to find and compare flights from Madison to Boston that are best for you.

Fly from

Madison

Fly to

Boston

Route

Depart

Return

Price

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 10/29

7:00 am-12:00 pm

1 stop4h 00m

Boston Logan Intl

Mon 11/3

5:45 am-10:18 am

1 stop5h 33m

$255

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 11/1

5:20 pm-11:49 pm

1 stop5h 29m

Boston Logan Intl

Mon 11/3

5:45 am-10:18 am

1 stop5h 33m

$255

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 11/1

5:20 pm-11:49 pm

1 stop5h 29m

Boston Logan Intl

Thu 11/6

5:34 am-8:40 am

1 stop4h 06m

$255

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 12/2

3:59 pm-9:45 pm

1 stop4h 46m

Boston Logan Intl

Tue 12/16

9:30 am-4:45 pm

2 stops8h 15m

$256

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 10/23

6:17 am-1:25 pm

1 stop6h 08m

Boston Logan Intl

Mon 10/27

6:25 pm-10:45 pm

1 stop5h 20m

$259

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 11/14

6:02 pm-11:55 pm

1 stop4h 53m

Boston Logan Intl

Mon 11/17

5:50 am-10:10 am

1 stop5h 20m

$259

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 9/27

5:26 pm-11:59 pm

1 stop5h 33m

Boston Logan Intl

Wed 10/1

8:00 am-2:27 pm

1 stop7h 27m

$270

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 10/22

1:19 pm-8:01 pm

1 stop5h 42m

Boston Logan Intl

Fri 10/24

5:34 am-10:45 am

1 stop6h 11m

$274

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 10/18

5:16 pm-11:49 pm

1 stop5h 33m

Boston Logan Intl

Thu 10/23

5:34 am-8:40 am

1 stop4h 06m

$275

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 10/28

5:21 pm-11:49 pm

1 stop5h 28m

Boston Logan Intl

Fri 10/31

10:30 am-2:25 pm

1 stop4h 55m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 24 results
1
2
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Best time to book a flight from Madison to Boston

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

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

Use this chart to determine the optimal time to book a round-trip flight from Madison to Boston. Price data was last updated on August 29, 2025.

To ensure you get the cheapest price possible for a flight from Madison to Boston, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, January is the cheapest month in which you can book a flight from Madison to Boston (average of $218). Flying from Madison to Boston 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 BOS?

Find hourly flight availability from Madison to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

It’s optimal to fly from Madison to Boston at noon. By choosing this option you can save up to 19% on the cost of your flight, compared to a flight in the morning.

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. 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 Boston. Reviews last updated September 11, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Madison to Boston by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

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
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

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
7,960 reviews

Crew

8.5

Food

7.3

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

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 Madison to Boston. 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 Madison to Boston?

    For as low as $255, Delta can have you in Boston from Madison in 4h. There are 929 mi between Madison and Boston. This flight may include one or multiple stops.

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

    Delta, at $250, was found to be the cheapest airline from Madison to Boston.Alternate airlines to your destination round-trip include American Airlines and United Airlines. These flights start at 42% lower than the current average price 3 months from now.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $100. Users have also found prices from $144 and $149 on United Airlines and Delta, respectively.

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

    Consider KLM (100%), Delta (100%) or American Airlines (0%) when booking your flight. These represent the most reliable airlines when flying from Madison to Boston.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Madison to Boston (average of $218). Flying from Madison to Boston 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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Waltham
Saugus
Burlington

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Top 3 airlines flying from Madison to Boston

Discover the top 3 airlines that operate flights from Madison to Boston. 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$250Average$493FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$253Average$387FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$286Average$463FlexibilityNo cancel feeOn-time69%

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