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$142+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — BOS
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Boston Logan Intl are usually found in January or September, booked 50 days in advance, depart on a Saturday or Wednesday and return on a Tuesday

Cheap 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 April 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:50 pm
MSN
-
BOS
2 stops37h 22m
Multiple Airlines
Wed 5/279:20 am
BOS
-
MSN
1 stop9h 05m
Multiple Airlines
Deal found 4/19$286
This Delta deal was found by Cheapflights users on 4/20. 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 9/124:00 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Sat 9/191:20 pm
BOS
-
MSN
Nonstop2h 53m
Delta
Deal found 4/20$313
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:05 pm
MSN
-
BOS
1 stop14h 07m
Multiple Airlines
Sat 5/910:07 am
BOS
-
MSN
2 stops47h 18m
Multiple Airlines
Deal found 4/20$315
This Delta deal was found by Cheapflights users on 4/19. 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 8/124:00 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Sat 8/155:40 am
BOS
-
MSN
1 stop6h 33m
Delta
Deal found 4/19$323
This United Airlines deal was found by Cheapflights users on 4/20. 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 8/125:00 am
MSN
-
BOS
1 stop5h 07m
United Airlines
Wed 8/196:00 am
BOS
-
MSN
1 stop4h 44m
United Airlines
Deal found 4/20$328
This Delta deal was found by Cheapflights users on 4/20. 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.
Mon 8/104:00 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Wed 8/191:20 pm
BOS
-
MSN
Nonstop2h 53m
Delta
Deal found 4/20$337
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:05 pm
MSN
-
BOS
1 stop14h 07m
Multiple Airlines
Tue 5/129:31 am
BOS
-
MSN
2 stops24h 43m
Multiple Airlines
Deal found 4/20$344
This Delta deal was found by Cheapflights users on 4/20. 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 7/112:30 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Wed 7/151:08 pm
BOS
-
MSN
Nonstop2h 55m
Delta
Deal found 4/20$346
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:50 pm
MSN
-
BOS
1 stop15h 16m
Multiple Airlines
Sun 5/106:00 am
BOS
-
MSN
2 stops27h 25m
Multiple Airlines
Deal found 4/18$348
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:50 pm
MSN
-
BOS
1 stop15h 16m
Multiple Airlines
Sun 5/316:00 am
BOS
-
MSN
2 stops27h 25m
Multiple Airlines
Deal found 4/19$349

Find 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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$286
(Kiwi.com)

One-way from

$142
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$431

Good round-trip deal

$390 or less

Good one-way deal

$251 or less
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. 11% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Madison Truax Field to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Madison Truax Field to Boston Logan Intl.
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 April 23, 2026.
Use the filters below to find and compare flights from Madison to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 8/12

4:00 pm-7:34 pm

Nonstop2h 34m

Boston Logan Intl

Sat 8/15

5:40 am-11:13 am

1 stop6h 33m

$323

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 7/4

9:30 am-4:09 pm

1 stop5h 39m

Boston Logan Intl

Sat 7/11

5:40 am-8:52 am

1 stop4h 12m

$333

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Mon 8/10

2:40 pm-10:20 pm

1 stop6h 40m

Boston Logan Intl

Wed 8/19

1:20 pm-3:13 pm

Nonstop2h 53m

$347

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 5/16

2:25 pm-9:59 pm

1 stop6h 34m

Boston Logan Intl

Sat 5/23

6:00 am-9:54 am

1 stop4h 54m

$367
Quickest round-trip

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sun 8/2

3:46 pm-7:20 pm

Nonstop2h 34m

Boston Logan Intl

Sat 8/8

5:40 am-8:52 am

1 stop4h 12m

$376

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 7/22

1:31 pm-8:00 pm

1 stop5h 29m

Boston Logan Intl

Mon 7/27

1:08 pm-3:03 pm

Nonstop2h 55m

$376

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 6/3

5:00 am-11:05 am

1 stop5h 05m

Boston Logan Intl

Sun 6/7

6:00 am-9:59 am

1 stop4h 59m

$382

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 8/5

6:30 am-2:40 pm

2 stops7h 10m

Boston Logan Intl

Tue 8/11

6:42 pm-12:04 am

1 stop6h 22m

$418

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 5/19

6:30 am-3:03 pm

1 stop7h 33m

Boston Logan Intl

Thu 5/28

6:00 am-2:57 pm

3 stops9h 57m

$447

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 6/3

6:15 pm-11:29 pm

1 stop4h 14m

Boston Logan Intl

Sun 6/7

1:08 pm-3:06 pm

Nonstop2h 58m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Boston flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 April 17, 2026.

To ensure you get the cheapest price possible for a flight from Madison to Boston, you should look to book at least 50 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 $306). Flying from Madison to Boston in March is currently the most expensive (average of $484). 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.

How much does it cost to fly round-trip from Madison to Boston?

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 April 23, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican 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
8,438 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,438 reviews
Delta
7.9
Good
8,438 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,637 reviews
Delta
7.9
Good
8,438 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,659 reviews
Delta
7.9
Good
8,438 reviews

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Crew

8.5

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 $323, Delta can have you in Boston from Madison in 2h 34m. 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?

    American Airlines, at $252, was found to be the cheapest airline from Madison to Boston.Alternate airlines to your destination round-trip include United Airlines and Delta. These flights start at 35% 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 $125. Users have also found prices from $129 and $148 on American Airlines and United Airlines, respectively.

  • What are the cheapest flights from Madison to Boston?

    Looking for the cheapest flight from Madison to Boston? While on average our users pay $623, our data indicates the cheapest price to be $203. The most popular route (Madison Truax Field - Boston Logan Intl), is priced around $313.

  • 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 $306). Flying from Madison to Boston in March is currently the most expensive (average of $484). 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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
Braintree

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$252Average$376FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$412FlexibilityNo cancel feeOn-time69%
DeltaCheapest$258Average$390FlexibilityNo cancel feeOn-timeN/A

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