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$127+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — BOS
May 8 — May 151
Fri 5/8
Fri 5/15
1 adult, Economy
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Find cheap flights from Madison to Boston with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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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 Monday

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 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/4. 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 4/4$289
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 5/156:50 pm
MSN
-
BOS
1 stop15h 16m
Multiple Airlines
Tue 5/269:12 am
BOS
-
MSN
2 stops33h 13m
Multiple Airlines
Deal found 4/4$305
This Delta deal was found by Cheapflights users on 4/5. 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 7/143:46 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Tue 7/211:08 pm
BOS
-
MSN
Nonstop2h 55m
Delta
Deal found 4/5$313
This Kiwi.com deal was found by Cheapflights users on 4/3. 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 4/3$332
This Delta deal was found by Cheapflights users on 4/7. 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 4/7$333
This Kiwi.com deal was found by Cheapflights users on 4/5. 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.
Sat 5/97:55 pm
MSN
-
BOS
1 stop12h 17m
Multiple Airlines
Tue 5/269:12 am
BOS
-
MSN
2 stops33h 13m
Multiple Airlines
Deal found 4/5$334
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 5/156:50 pm
MSN
-
BOS
1 stop15h 16m
Multiple Airlines
Wed 5/2010:07 am
BOS
-
MSN
1 stop8h 18m
Multiple Airlines
Deal found 4/4$336

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 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$289
(Kiwi.com)

One-way from

$127
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$412

Good round-trip deal

$358 or less

Good one-way deal

$222 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. 10% potential increase in price ($47 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 8, 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

Tue 6/30

3:46 pm-7:25 pm

Nonstop2h 39m

Boston Logan Intl

Sat 7/4

11:10 am-1:02 pm

Nonstop2h 52m

$313

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 8/18

2:40 pm-10:20 pm

1 stop6h 40m

Boston Logan Intl

Sat 8/22

1:20 pm-3:13 pm

Nonstop2h 53m

$323

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 8/12

1:45 pm-7:45 pm

1 stop5h 00m

Boston Logan Intl

Sat 8/15

5:40 am-11:13 am

1 stop6h 33m

$333

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 9/12

2:40 pm-10:20 pm

1 stop6h 40m

Boston Logan Intl

Sat 9/19

5:40 am-11:13 am

1 stop6h 33m

$333
Quickest round-trip

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Mon 8/10

4:25 pm-7:59 pm

Nonstop2h 34m

Boston Logan Intl

Wed 8/19

1:54 pm-3:47 pm

Nonstop2h 53m

$337

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 7/9

3:05 pm-11:31 pm

1 stop7h 26m

Boston Logan Intl

Wed 7/15

1:08 pm-3:03 pm

Nonstop2h 55m

$347

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 7/22

7:00 am-2:23 pm

1 stop6h 23m

Boston Logan Intl

Mon 7/27

5:55 am-11:19 am

1 stop6h 24m

$357

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 7/3

3:10 pm-11:27 pm

1 stop7h 17m

Boston Logan Intl

Mon 7/6

5:30 am-8:50 am

1 stop4h 20m

$381

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 7/29

3:46 pm-7:20 pm

Nonstop2h 34m

Boston Logan Intl

Fri 8/7

1:08 pm-3:03 pm

Nonstop2h 55m

$386

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 5/12

2:30 pm-9:59 pm

1 stop6h 29m

Boston Logan Intl

Sat 5/23

6:00 am-7:02 pm

3 stops14h 02m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/3

Showing 1-10 of 23 resultsSorted by cheapest first
1
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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 3, 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, September is the cheapest month in which you can book a flight from Madison to Boston (average of $93). Flying from Madison to Boston in November is currently the most expensive (average of $206). 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 8, 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
8,388 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

7.9

Food

7.2

Overall

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
8,388 reviews
Delta
7.9
Good
8,388 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

7.9

Food

7.2

Overall

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
9,551 reviews
Delta
7.9
Good
8,388 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

7.9

Food

7.2

Overall

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
11,548 reviews
Delta
7.9
Good
8,388 reviews

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

7.9

Food

7.2

Overall

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 $313, Delta can have you in Boston from Madison in 2h 39m. There are 929 mi between Madison and Boston. All flights are typically nonstop.

  • 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 Delta and United Airlines. These flights start at 34% 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 $609, 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, September is the cheapest month in which you can book a flight from Madison to Boston (average of $93). Flying from Madison to Boston in November is currently the most expensive (average of $206). 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
Seabrook
Warwick
Peabody
York Beach
Londonderry
Swansea
Old Orchard Beach
Lincoln
Quincy
Waltham
Lowell

Browse thousands of different options on Cheapflights for your next trip

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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 April 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$252Average$373FlexibilityNo cancel feeOn-time71%
DeltaCheapest$253Average$389FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$254Average$414FlexibilityNo cancel feeOn-time69%

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