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$126+ 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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — BOS
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Madison Truax Field to Boston Logan Intl are usually found in August or September, booked 57 days in advance, depart on a Wednesday or Monday and return on a Monday

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 October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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 12/1710:20 amMSN - BOS
1 stop5h 03mAmerican Airlines
Sun 1/184:20 pmBOS - MSN
1 stop7h 39mAmerican Airlines
Deal found 10/26$255
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 12/121:35 pmMSN - BOS
1 stop5h 25mDelta
Sun 12/146:24 pmBOS - MSN
1 stop5h 33mDelta
Deal found 10/28$259
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/68:15 amMSN - BOS
2 stops9h 33mUnited Airlines
Sun 12/76:00 amBOS - MSN
1 stop5h 14mUnited Airlines
Deal found 10/28$260
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:30 amMSN - BOS
1 stop5h 13mUnited Airlines
Mon 12/155:30 amBOS - MSN
2 stops7h 14mUnited Airlines
Deal found 10/26$264
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:26 pmMSN - BOS
1 stop6h 19mUnited Airlines
Fri 1/27:45 amBOS - MSN
1 stop5h 03mUnited Airlines
Deal found 10/26$265
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/154:34 pmMSN - BOS
1 stop6h 09mAmerican Airlines
Sat 11/225:40 amBOS - MSN
1 stop5h 10mAmerican Airlines
Deal found 10/26$270
This Delta deal was found by Cheapflights users on 10/25. 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 11/136:12 amMSN - BOS
1 stop6h 11mDelta
Sun 11/165:29 amBOS - MSN
1 stop4h 29mDelta
Deal found 10/25$274
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 11/121:30 pmMSN - BOS
1 stop5h 30mDelta
Sat 11/155:29 amBOS - MSN
1 stop4h 23mDelta
Deal found 10/28$289
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/128:25 amMSN - BOS
1 stop4h 43mUnited Airlines
Sat 11/1510:18 amBOS - MSN
2 stops8h 32mUnited Airlines
Deal found 10/28$294
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/133:55 pmMSN - BOS
1 stop4h 50mUnited Airlines
Sun 12/145:30 amBOS - MSN
2 stops7h 14mUnited Airlines
Deal found 10/28$304
This Delta deal was found by Cheapflights users on 10/28. 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.
Tue 11/116:07 pmMSN - BOS
1 stop4h 48mDelta
Fri 11/145:50 amBOS - MSN
1 stop5h 21mDelta
Deal found 10/28$307

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$255
(American Airlines)

One-way from

$126
(United Airlines)

Popular in

February

Cheapest in

August

Average price

$378
Provider with most accurate pricing for Madison Truax Field-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Boston Logan Intl flights.
Search Deals
From Madison Truax Field to Boston Logan Intl
Search Deals
One-way flight from Madison Truax Field to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 28, 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

Sat 12/13

5:58 pm-11:14 pm

1 stop4h 16m

Boston Logan Intl

Sun 12/14

6:24 pm-10:57 pm

1 stop5h 33m

$255

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 12/16

4:02 pm-11:44 pm

1 stop6h 42m

Boston Logan Intl

Sun 1/18

6:00 am-10:19 am

1 stop5h 19m

$255

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 12/18

10:45 am-7:18 pm

1 stop7h 33m

Boston Logan Intl

Sun 1/18

6:00 am-10:19 am

1 stop5h 19m

$259

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 12/12

1:35 pm-8:00 pm

1 stop5h 25m

Boston Logan Intl

Sun 12/14

6:24 pm-10:57 pm

1 stop5h 33m

$259

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 12/12

9:49 am-6:11 pm

1 stop7h 22m

Boston Logan Intl

Sun 12/14

6:36 pm-11:49 pm

1 stop6h 13m

$259

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 12/12

6:30 am-12:43 pm

1 stop5h 13m

Boston Logan Intl

Mon 12/15

5:30 am-11:44 am

2 stops7h 14m

$264

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Mon 12/29

5:26 pm-12:45 am

1 stop6h 19m

Boston Logan Intl

Fri 1/2

7:45 am-11:48 am

1 stop5h 03m

$265

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 11/13

6:12 am-1:23 pm

1 stop6h 11m

Boston Logan Intl

Sun 11/16

5:29 am-8:58 am

1 stop4h 29m

$274

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 11/12

3:37 pm-10:20 pm

1 stop5h 43m

Boston Logan Intl

Sun 11/16

6:00 am-10:22 am

1 stop5h 22m

$289

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 11/12

8:25 am-2:08 pm

1 stop4h 43m

Boston Logan Intl

Sat 11/15

10:18 am-5:50 pm

2 stops8h 32m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 20 results
1
2

Compare providers for flights from Madison to Boston

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 Madison to Boston in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*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 Madison-Boston flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Madison-Boston flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Madison-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Boston flights, Cheapflights users trust eDreams the most. eDreams 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 Madison-Boston 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 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 October 24, 2025.

To ensure you get the cheapest price possible for a flight from Madison to Boston, you should look to book at least 57 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, October is the cheapest month in which you can book a flight from Madison to Boston (average of $88). Flying from Madison to Boston in January is currently the most expensive (average of $222). 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 October 28, 2025.

It’s optimal to fly from Madison to Boston in the afternoon. By choosing this option you can save up to 48% 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 October 28, 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
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Comfort

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 16m. 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 41% 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 Delta. According to our data, you can fly for as low as $126. Users have also found prices from $126 and $126 on United Airlines and American Airlines, 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, October is the cheapest month in which you can book a flight from Madison to Boston (average of $88). Flying from Madison to Boston in January is currently the most expensive (average of $222). 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
Peabody
Quincy
York Beach
Warwick
Swansea
Old Orchard Beach
Brockton
Waltham
Chelsea

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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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$250Average$484FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$252Average$384FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$258Average$432FlexibilityNo cancel feeOn-time69%

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