$164 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 6/23. 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
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Cheap Flights from Madison to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$279
Albany
Albany1 stop$280
Boston
Boston1 stop$279
Albany
Albany1 stop$280

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

Wed, Feb 25 - Wed, Mar 4
United Airlines Logo
8:15 am - 2:10 pm
MSN
-
BDL
4h 55m
1 stop
United Airlines Logo
10:05 am - 2:07 pm
BDL
-
MSN
5h 02m
1 stop
$269United Airlines
Wed, May 13 - Wed, May 20
United Airlines Logo
2:30 pm - 11:45 pm
MSN
-
BDL
8h 15m
2 stops
United Airlines Logo
5:00 pm - 9:15 pm
BDL
-
MSN
5h 15m
1 stop
$274United Airlines
Fri, Apr 3 - Tue, Apr 7
United Airlines Logo
6:30 am - 12:46 pm
MSN
-
BOS
5h 16m
1 stop
United Airlines Logo
7:15 am - 11:38 am
BOS
-
MSN
5h 23m
1 stop
$279United Airlines
Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
4:20 pm - 11:44 pm
MSN
-
ALB
6h 24m
1 stop
American Airlines Logo
5:07 pm - 10:00 pm
ALB
-
MSN
5h 53m
1 stop
$280American Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
10:44 am - 6:24 pm
MSN
-
BOS
6h 40m
1 stop
American Airlines Logo
5:40 am - 10:55 am
BOS
-
MSN
6h 15m
1 stop
$293American Airlines
Wed, Mar 11 - Mon, Mar 16
American Airlines Logo
7:00 am - 1:02 pm
MSN
-
ALB
5h 02m
1 stop
American Airlines Logo
5:28 pm - 11:35 pm
ALB
-
MSN
7h 07m
1 stop
$295American Airlines
Mon, Mar 2 - Sat, Mar 7
American Airlines Logo
8:09 am - 2:44 pm
MSN
-
BOS
5h 35m
1 stop
American Airlines Logo
7:02 pm - 11:40 pm
BOS
-
MSN
5h 38m
1 stop
$296American Airlines
Thu, Jun 18 - Mon, Jun 22
Delta Logo
4:45 pm - 8:19 pm
MSN
-
BOS
2h 34mnonstop
Delta Logo
2:00 pm - 3:53 pm
BOS
-
MSN
2h 53mnonstop
$309Delta
Sat, Mar 14 - Thu, Mar 19
Delta Logo
5:30 am - 12:07 pm
MSN
-
ALB
5h 37m
1 stop
Delta Logo
6:00 am - 8:51 am
ALB
-
MSN
3h 51m
1 stop
$314Delta
Thu, Feb 19 - Sun, Feb 22
Delta Logo
8:00 am - 3:33 pm
MSN
-
ORH
6h 33m
1 stop
Delta Logo
4:30 pm - 10:48 pm
ORH
-
MSN
7h 18m
2 stops
$335Delta
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 $273 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 $273.

Can I save money by flying with a layover from Madison to Massachusetts?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $338 on average.

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 September, 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 $473 and $467 respectively.

What’s the cheapest day of the week to fly from Madison to Massachusetts?

The average price of all round-trip flights from Madison to Massachusetts clicked on KAYAK for each day over the last 12 months.

When flying from Madison to Massachusetts, you should consider leaving on a Saturday and avoid Mondays if you are looking for the best rates. For your return to Madison, you’ll find the best rates on Fridays and the most expensive ones on Sundays.

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 4 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$164
Most popular time to fly and prices are also 17% 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 evening, when round-trip flights cost $349 on average. Morning departures are around 27% more expensive than evening flights, 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 $443.

Top tips for finding cheap flights to Massachusetts

  • Looking for a cheap flight? 25% of our users found tickets from Madison to the following destinations at these prices or less: Boston $256 one-way - $349 round-trip

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 8127 reviews
7.2Food
7.8Entertainment
7.9Comfort
8.1Boarding
8.5Crew
Airline reviews

Timing, quality of service, promptness and courtesy of the staff

10.0 ExcellentAjai, Jan 2026
DFW - ATL
Read more Delta reviews

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The flight crew where really good. Better then the crew from BNE to SFO

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

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

Information on your arrival and departure airports