$126 Find Cheap Flights from Madison to Massachusetts

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Massachusetts departing on 12/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to Massachusetts, as well as popular online travel agencies
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Madison to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$255
Albany
Albany1 stop$264
Boston
Boston1 stop$255
Albany
Albany1 stop$264

Book Cheap Madison to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Massachusetts

Tue, Dec 9 - Sat, Dec 13
United Airlines Logo
6:30 am - 2:16 pmMSN-BDL
6h 46m1 stop
United Airlines Logo
6:10 am - 10:14 amBDL-MSN
5h 04m1 stop
$249United Airlines
Find Deal
Tue, Dec 9 - Sat, Dec 13
United Airlines Logo
2:48 pm - 11:59 pmMSN-BDL
8h 11m2 stops
United Airlines Logo
6:10 am - 10:14 amBDL-MSN
5h 04m1 stop
$254United Airlines
Find Deal
Wed, Dec 17 - Tue, Dec 30
Delta Logo
6:12 am - 12:15 pmMSN-BOS
5h 03m1 stop
Delta Logo
5:45 am - 10:10 amBOS-MSN
5h 25m1 stop
$255Delta
Find Deal
Thu, Mar 12 - Wed, Mar 18
Delta Logo
7:00 am - 12:23 pmMSN-BOS
4h 23m1 stop
Delta Logo
3:05 pm - 10:08 pmBOS-MSN
8h 03m1 stop
$259Delta
Find Deal
Fri, Feb 6 - Sun, Feb 8
United Airlines Logo
3:48 pm - 11:44 pmMSN-BDL
6h 56m2 stops
United Airlines Logo
6:00 am - 2:10 pmBDL-MSN
9h 10m2 stops
$259United Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 31
United Airlines Logo
3:59 pm - 11:41 pmMSN-BOS
6h 42m2 stops
United Airlines Logo
9:30 am - 3:05 pmBOS-MSN
6h 35m1 stop
$260United Airlines
Find Deal
Sat, Nov 22 - Wed, Dec 3
United Airlines Logo
6:20 am - 12:06 pmMSN-ALB
4h 46m1 stop
United Airlines Logo
6:00 am - 11:44 amALB-MSN
6h 44m1 stop
$264United Airlines
Find Deal
Wed, Dec 17 - Wed, Dec 31
American Airlines Logo
6:09 am - 3:05 pmMSN-ORH
7h 56m2 stops
American Airlines Logo
12:19 pm - 10:08 amORH-MSN
22h 49m2 stops
$267American Airlines
Find Deal
Tue, Dec 16 - Sun, Jan 18
American Airlines Logo
8:11 am - 2:47 pmMSN-BOS
5h 36m1 stop
American Airlines Logo
6:00 am - 10:19 amBOS-MSN
5h 19m1 stop
$280American Airlines
Find Deal
Tue, Nov 25 - Tue, Dec 2
Multiple Airlines Logo
9:48 am - 4:50 pmMSN-BOS
30h 02m2 stops
Multiple Airlines Logo
5:45 pm - 5:28 pmBOS-MSN
24h 43m1 stop
$405Multiple Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Madison to Massachusetts flights

Get data-powered insights and trends into flights from Madison to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Madison to Massachusetts flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Massachusetts from Madison found in the last 72 hours was to Boston, at $267 round-trip. The most popular route is from Madison (MSN) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $267.

What is the cheapest month to fly from Madison to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to Massachusetts is August, when tickets cost $318 (return) on average. On the other hand, the most expensive months are February and March, when the average cost of round-trip tickets is $578 and $488 respectively.

How far in advance should I book a flight from Madison to Massachusetts?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Madison to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Madison to Massachusetts, you should book around 6 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$126
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly and prices are also 26% lower on average.
Flight from Madison to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Madison to Massachusetts?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Massachusetts?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Madison to Massachusetts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Massachusetts?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Madison to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the afternoon, when round-trip flights cost $422 on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $516.

Reviews of the top 3 airlines serving from Madison to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Madison to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to Massachusetts? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8004 reviews
7.9Entertainment
8.1Boarding
8.5Crew
7.3Food
7.9Comfort
Airline reviews

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

2.0 MediocreAnonymous, Nov 2025MOB - ATL
Read more Delta reviews

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

Premium Plus is a really good idea for longer flights

7 hours delayed due to operational issues on United’s end. Basically laziness.

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Everything you need to know for your flight from Madison to Massachusetts

Information on your arrival and departure airports