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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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — BOS
Jul 19 — Jul 261
Sat 7/19
Sat 7/26
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 Tuesday

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 14, 2025.

Round-trip from

$251
(Delta)

One-way from

$126
(Delta)

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 ($68 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 14, 2025.

This Delta deal was found by Cheapflights users on 7/14. 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 9/135:26 pmMSN - BOS
1 stop5h 33mDelta
Tue 9/1610:30 amBOS - MSN
1 stop4h 57mDelta
Deal found 7/14$251
This American Airlines deal was found by Cheapflights users on 7/12. 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 8/79:48 amMSN - BOS
1 stop6h 02mAmerican Airlines
Tue 8/125:28 amBOS - MSN
1 stop4h 43mAmerican Airlines
Deal found 7/12$255
This United Airlines deal was found by Cheapflights users on 7/12. 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.
Tue 8/263:58 pmMSN - BOS
1 stop4h 30mUnited Airlines
Wed 9/39:05 amBOS - MSN
2 stops6h 57mUnited Airlines
Deal found 7/12$256

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 14, 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

5:26 pm-11:59 pm

1 stop5h 33m

Boston Logan Intl

Tue 9/16

10:30 am-2:27 pm

1 stop4h 57m

$251

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 10/3

2:16 pm-8:41 pm

1 stop5h 25m

Boston Logan Intl

Tue 10/7

8:00 am-1:10 pm

1 stop6h 10m

$255

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 8/26

3:58 pm-9:28 pm

1 stop4h 30m

Boston Logan Intl

Wed 9/3

9:05 am-3:02 pm

2 stops6h 57m

$256

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 8/12

6:00 am-2:14 pm

1 stop7h 14m

$126

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Mon 8/11

3:55 pm-11:59 pm

1 stop7h 04m

$130

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Tue 8/12

2:35 pm-11:10 pm

2 stops7h 35m

$131

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Fri 8/22

7:59 pm-11:14 am

2 stops14h 15m

$203

MadisonBoston

MSN - BOS

MSNBOS

Madison Truax Field

Sat 8/16

10:19 am-11:12 pm

2 stops11h 53m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/11

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 11, 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 $307). 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 14, 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.

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 July 14, 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
8.0
Very good
7,953 reviews

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,953 reviews
Delta
8.0
Very good
7,953 reviews

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,856 reviews
Delta
8.0
Very good
7,953 reviews

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,953 reviews

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Frontier
5.9
Fair
3,261 reviews
Delta
8.0
Very good
7,953 reviews

Food

7.3

Overall

8.0

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 Delta. According to our data, you can fly for as low as $126. Users have also found prices from $130 and $161 on American Airlines 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 $307). 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
Smithfield
Cranston
Randolph
Chestnut Hill
Brockton
York Beach
Chelsea
Saco
Burlington
Hampton Beach
Swansea
Lincoln

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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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$257Average$487FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$257Average$403FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$297Average$450FlexibilityNo cancel feeOn-time69%

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