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$164+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — BOS
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 57 days in advance, depart on a Wednesday or Monday 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 January 27, 2026.

This Delta deal was found by Cheapflights users on 1/27. 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.
Tue 9/224:45 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Wed 9/302:00 pm
BOS
-
MSN
Nonstop2h 53m
Delta
Deal found 1/27$273
This Delta deal was found by Cheapflights users on 1/27. 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.
Fri 10/304:45 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Sat 11/72:00 pm
BOS
-
MSN
Nonstop2h 53m
Delta
Deal found 1/27$276
This Delta deal was found by Cheapflights users on 1/27. 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 10/294:45 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Fri 11/62:00 pm
BOS
-
MSN
Nonstop2h 53m
Delta
Deal found 1/27$279
This Delta deal was found by Cheapflights users on 1/27. 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.
Sat 9/124:45 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Sat 9/195:30 am
BOS
-
MSN
1 stop4h 16m
Delta
Deal found 1/27$283
This United Airlines deal was found by Cheapflights users on 1/26. 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 4/36:30 am
MSN
-
BOS
1 stop5h 16m
United Airlines
Tue 4/75:45 am
BOS
-
MSN
2 stops6h 53m
United Airlines
Deal found 1/26$284
This Delta deal was found by Cheapflights users on 1/27. 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.
Sat 8/154:45 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Thu 8/205:30 am
BOS
-
MSN
1 stop4h 16m
Delta
Deal found 1/27$286
This Delta deal was found by Cheapflights users on 1/27. 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.
Fri 9/114:45 pm
MSN
-
BOS
Nonstop2h 34m
Delta
Mon 9/213:00 pm
BOS
-
MSN
1 stop6h 13m
Delta
Deal found 1/27$289
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/2210:44 am
MSN
-
BOS
1 stop6h 40m
American Airlines
Wed 4/295:40 am
BOS
-
MSN
1 stop6h 15m
American Airlines
Deal found 1/27$293
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/143:53 pm
MSN
-
BOS
1 stop4h 55m
United Airlines
Wed 2/1812:35 pm
BOS
-
MSN
1 stop5h 28m
United Airlines
Deal found 1/27$294
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/88:00 am
MSN
-
BOS
1 stop5h 18m
American Airlines
Tue 5/1210:00 am
BOS
-
MSN
1 stop6h 41m
American Airlines
Deal found 1/27$296
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/304:12 pm
MSN
-
BOS
1 stop6h 47m
American Airlines
Mon 5/47:18 pm
BOS
-
MSN
1 stop4h 56m
American Airlines
Deal found 1/27$299

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(United Airlines)

One-way from

$164
(Delta)

Popular in

February

Cheapest in

September

Average price

$397

Good round-trip deal

$349 or less

Good one-way deal

$256 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. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 January 27, 2026.
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 5/30

2:35 pm-9:40 pm

1 stop6h 05m

Boston Logan Intl

Thu 6/4

6:00 am-11:43 am

1 stop6h 43m

$279

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 4/3

6:30 am-12:46 pm

1 stop5h 16m

Boston Logan Intl

Tue 4/7

5:45 am-11:38 am

2 stops6h 53m

$284

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 2/14

3:53 pm-9:48 pm

1 stop4h 55m

Boston Logan Intl

Wed 2/18

12:35 pm-5:03 pm

1 stop5h 28m

$294

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 2/18

5:00 am-10:46 am

1 stop4h 46m

Boston Logan Intl

Tue 2/24

4:20 pm-10:42 pm

1 stop7h 22m

$296

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Mon 3/2

8:09 am-2:44 pm

1 stop5h 35m

Boston Logan Intl

Sat 3/7

7:02 pm-11:40 pm

1 stop5h 38m

$296

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 2/19

4:16 pm-11:59 pm

1 stop6h 43m

Boston Logan Intl

Mon 2/23

3:15 pm-9:58 pm

1 stop7h 43m

$299

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 7/17

4:45 pm-8:19 pm

Nonstop2h 34m

Boston Logan Intl

Sat 7/25

2:00 pm-3:53 pm

Nonstop2h 53m

$309

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 6/18

4:45 pm-8:19 pm

Nonstop2h 34m

Boston Logan Intl

Mon 6/22

2:00 pm-3:53 pm

Nonstop2h 53m

$309

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 7/25

4:45 pm-8:19 pm

Nonstop2h 34m

$164

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 7/22

4:45 pm-8:19 pm

Nonstop2h 34m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 17 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 January.
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 January 23, 2026.

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 December is currently the most expensive (average of $217). 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.

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 January 27, 2026.
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
8,119 reviews

Comfort

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Crew

8.5

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
8,119 reviews
Delta
7.9
Good
8,119 reviews

Comfort

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Crew

8.5

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
9,205 reviews
Delta
7.9
Good
8,119 reviews

Comfort

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Crew

8.5

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
7.2
Good
11,197 reviews
Delta
7.9
Good
8,119 reviews

Comfort

7.9

Boarding

8.1

Food

7.2

Entertainment

7.8

Crew

8.5

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 $296, United Airlines can have you in Boston from Madison in 4h 46m. 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 $199, 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 49% 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 $138 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 $366, our data indicates the cheapest price to be $223. The most popular route (Madison Truax Field - Boston Logan Intl), is priced around $279.

  • 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 December is currently the most expensive (average of $217). 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
Hampton Beach
Watertown
Seekonk
Brockton
Warwick
Seabrook
Cranston
Lincoln
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$199Average$384FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$253Average$375FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$254Average$396FlexibilityNo cancel feeOn-time69%

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