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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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — BOS
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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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 80 days in advance, depart on a Tuesday or Friday 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 July 29, 2025.

Round-trip from

$251
(Delta)

One-way from

$100
(American Airlines)

Popular in

February

Cheapest in

August

Average price

$388
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. 13% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 9/1310:55 amMSN - BOS
1 stop7h 48mDelta
Tue 9/163:00 pmBOS - MSN
1 stop7h 23mDelta
Deal found 7/28$251
This American Airlines deal was found by Cheapflights users on 7/27. 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 8/86:06 amMSN - BOS
1 stop5h 19mAmerican Airlines
Fri 8/227:25 amBOS - MSN
Nonstop2h 59mAmerican Airlines
Deal found 7/27$254
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 9/185:43 pmMSN - BOS
1 stop6h 02mUnited Airlines
Mon 9/226:10 amBOS - MSN
1 stop4h 35mUnited Airlines
Deal found 7/28$273

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 July 29, 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 9/13

10:55 am-7:43 pm

1 stop7h 48m

Boston Logan Intl

Tue 9/16

3:00 pm-9:23 pm

1 stop7h 23m

$251

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 8/8

6:06 am-12:25 pm

1 stop5h 19m

Boston Logan Intl

Fri 8/22

7:25 am-9:24 am

Nonstop2h 59m

$254

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Thu 9/18

5:43 pm-12:45 am

1 stop6h 02m

Boston Logan Intl

Mon 9/22

6:10 am-9:45 am

1 stop4h 35m

$273

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sun 8/31

6:19 am-12:11 pm

1 stop4h 52m

$100

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 8/19

6:00 am-12:20 pm

1 stop5h 20m

$126

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 9/9

10:50 am-6:55 pm

2 stops7h 05m

$131

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Wed 8/20

10:19 am-11:18 am

2 stops23h 59m

$258

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Mon 10/27

2:25 pm-10:41 am

2 stops19h 16m

$282

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 9/12

7:15 am-5:55 pm

2 stops33h 40m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 25, 2025.

To ensure you get the cheapest price possible for a flight from Madison to Boston, you should look to book at least 80 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 July 29, 2025.

It’s optimal to fly from Madison to Boston in the afternoon. By choosing this option you can save up to 28% 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 July 29, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Delta, and United 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Sun Country Air
6.9
Okay
333 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Boarding

8.1

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

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

    Delta, at $251, 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 $126 and $131 on Delta and United Airlines, respectively.

  • 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
Watertown
Warwick
Seabrook
Waltham
Framingham
Lowell
Randolph
Smithfield
Cranston
Chestnut Hill
York Beach
Chelsea
Saco
Burlington
Hampton Beach
Swansea
Lincoln
Quincy

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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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$254Average$396FlexibilityNo cancel feeOn-time71%
DeltaCheapest$255Average$490FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$297Average$455FlexibilityNo cancel feeOn-time69%

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