$100 Cheap Flights from Madison (MSN) to Boston (BOS)

View $100 flight on Sun, Aug 31, 2025Opens in a new window

Popular airlines from Dane County Regional Airport (MSN) to Logan International Airport (BOS)

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

Cheap Flights from Madison to Boston (MSN-BOS)

Prices were available within the past 7 days and start at $100 for one-way flights and $225 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Aug 23 - Sun, Aug 31
MSN
Madison
BOS
Boston
$225 Roundtrip, just found
$225
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 23 from Madison to Boston, returning Sun, Aug 31, priced at $225 just found
United
Thu, Nov 27 - Wed, Dec 3
MSN
Madison
BOS
Boston
$225 Roundtrip, found 9 hours ago
$225
Roundtrip
found 9 hours ago
Select United flight, departing Thu, Nov 27 from Madison to Boston, returning Wed, Dec 3, priced at $225 found 9 hours ago
American Airlines
Thu, Nov 27 - Wed, Dec 3
MSN
Madison
BOS
Boston
$226 Roundtrip, found 9 hours ago
$226
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Nov 27 from Madison to Boston, returning Wed, Dec 3, priced at $226 found 9 hours ago
American Airlines
Sat, Aug 23 - Sun, Aug 31
MSN
Madison
BOS
Boston
$228 Roundtrip, just found
$228
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 23 from Madison to Boston, returning Sun, Aug 31, priced at $228 just found
United
Thu, Nov 27 - Wed, Dec 3
MSN
Madison
BOS
Boston
$230 Roundtrip, found 9 hours ago
$230
Roundtrip
found 9 hours ago
Select United flight, departing Thu, Nov 27 from Madison to Boston, returning Wed, Dec 3, priced at $230 found 9 hours ago
United
Thu, Nov 27 - Wed, Dec 3
MSN
Madison
BOS
Boston
$232 Roundtrip, found 9 hours ago
$232
Roundtrip
found 9 hours ago
Select United flight, departing Thu, Nov 27 from Madison to Boston, returning Wed, Dec 3, priced at $232 found 9 hours ago
United
Fri, Oct 31 - Mon, Nov 3
MSN
Madison
BOS
Boston
$234 Roundtrip, found 13 hours ago
$234
Roundtrip
found 13 hours ago
Select United flight, departing Fri, Oct 31 from Madison to Boston, returning Mon, Nov 3, priced at $234 found 13 hours ago
United
Thu, Nov 27 - Wed, Dec 3
MSN
Madison
BOS
Boston
$235 Roundtrip, found 9 hours ago
$235
Roundtrip
found 9 hours ago
Select United flight, departing Thu, Nov 27 from Madison to Boston, returning Wed, Dec 3, priced at $235 found 9 hours ago
United
Thu, Nov 27 - Wed, Dec 3
MSN
Madison
BOS
Boston
$237 Roundtrip, found 9 hours ago
$237
Roundtrip
found 9 hours ago
Select United flight, departing Thu, Nov 27 from Madison to Boston, returning Wed, Dec 3, priced at $237 found 9 hours ago
Delta
Tue, Aug 26 - Sun, Aug 31
MSN
Madison
BOS
Boston
$244 Roundtrip, found 5 hours ago
$244
Roundtrip
found 5 hours ago
Select Delta flight, departing Tue, Aug 26 from Madison to Boston, returning Sun, Aug 31, priced at $244 found 5 hours ago

Find the cheapest month to fly from Madison (MSN) to Boston (BOS)

August is typically the cheapest month to fly

From $245 - $441 per traveler.

Graph displaying average flight prices per month

Alternative airports near Boston

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Logan Intl. BOS. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $351
BOS
Logan Intl.
CheapestClosest
Average driving time to city center7 min
Flights from $351
Flights from Madison (MSN) to Boston (BOS)
Origin airport
Dane County Regional
Destination airport
Logan Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$224
Distance
929 mi

Madison to Boston Flights

The cheapest times to fly from Madison to Boston

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Madison to Boston are during the month of August. You can find some of the cheapest flights from Madison to Boston with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Madison to Boston

Sunday is one of the best days to book for cheap flights from Madison to Boston: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Madison to Boston

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Madison to Boston in 2025. You can also book with separate airlines for your outbound and return journeys, from $100 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Madison to Boston flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Madison to Boston airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS) cost?
Grab cheap return flights starting from $399 from Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Delta flight leaving MSN on August 17 2025 and touching down at BOS. The price was last updated on July 23 2025 and has not changed since.
What is the cheapest month to fly from MSN to BOS?
The cheapest flights from MSN to BOS are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from MSN to BOS?
With prices as low as $150 for a one-way flight from MSN to BOS, American Airlines is currently the cheapest airline flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MSN on August 21 2025. Prices were last updated on July 23 2025 and have not changed since.
How many flights per day from Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS)?
You'll need to take a flight with a layover if you're traveling from Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS). There are no daily direct flights on this route. However, simply filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from MSN to BOS?
Friday is generally the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can vary based on a number of factors, such as the time of year and carrier.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from MSN to BOS?
Consider booking with United Airlines if you'd like to go straight from Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS) without any interruptions. This carrier has the best track record for punctuality, with an on-time performance of 100%. Want to get notified of any changes? You can check your flight status using the Expedia App.
What is the best time to fly from Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS)?
To avoid possible delays on the Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS) route, fly before 3 PM. Flights after this time have a 22% higher chance of cancellation.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS) last-minute?
Last-minute fares from MSN to BOS are generally more expensive. For the lowest prices, start looking for flights well ahead of time. That being said, if you can play around with your travel dates, you may find a cheap ticket right before your trip.
Is it cheaper to book a MSN to BOS flight and hotel package?
Booking a MSN to BOS flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our wide range of hotels and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Dane County Regional Airport (MSN) to Logan Intl. Airport (BOS)?
If you booked your MSN to BOS flight in the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

Explore a world of travel with Expedia

*Available to One Key members.