$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 7/20. 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$265
Albany
Albany1 stop$269
Boston
Boston1 stop$265
Albany
Albany1 stop$269

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 18 - Wed, Feb 25
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
$262Delta
Wed, Feb 18 - Tue, Feb 24
American Airlines Logo
3:03 pm - 11:59 pm
MSN
-
BOS
7h 56m
1 stop
American Airlines Logo
12:09 pm - 8:56 pm
BOS
-
MSN
9h 47m
1 stop
$265American Airlines
Wed, Feb 18 - Tue, Feb 24
Delta Logo
7:00 am - 3:33 pm
MSN
-
ORH
7h 33m
2 stops
Delta Logo
4:30 pm - 10:48 pm
ORH
-
MSN
7h 18m
2 stops
$268Delta
Wed, Feb 25 - Wed, Mar 4
United Airlines Logo
8:15 am - 2:05 pm
MSN
-
ALB
4h 50m
1 stop
United Airlines Logo
10:10 am - 2:57 pm
ALB
-
MSN
5h 47m
1 stop
$269United Airlines
Wed, Apr 1 - Wed, Apr 8
United Airlines Logo
8:30 am - 2:15 pm
MSN
-
BDL
4h 45m
1 stop
United Airlines Logo
6:00 am - 11:38 am
BDL
-
MSN
6h 38m
1 stop
$269United Airlines
Sat, Jun 20 - Tue, Jun 23
Delta Logo
4:45 pm - 8:19 pm
MSN
-
BOS
2h 34mnonstop
Delta Logo
2:00 pm - 3:53 pm
BOS
-
MSN
2h 53mnonstop
$273Delta
Wed, Apr 1 - Wed, Apr 8
United Airlines Logo
6:00 am - 2:08 pm
MSN
-
BDL
7h 08m
2 stops
United Airlines Logo
5:05 pm - 9:16 pm
BDL
-
MSN
5h 11m
1 stop
$274United Airlines
Thu, Jun 18 - Wed, Jun 24
Delta Logo
4:45 pm - 8:19 pm
MSN
-
BOS
2h 34mnonstop
Delta Logo
2:00 pm - 3:53 pm
BOS
-
MSN
2h 53mnonstop
$276Delta
Fri, Feb 6 - Sun, Feb 8
American Airlines Logo
4:47 pm - 10:34 pm
MSN
-
ALB
4h 47m
1 stop
American Airlines Logo
6:25 pm - 11:41 pm
ALB
-
MSN
6h 16m
1 stop
$279American Airlines
Tue, Feb 10 - Tue, Feb 17
American Airlines Logo
11:29 am - 8:45 pm
MSN
-
BOS
8h 16m
1 stop
American Airlines Logo
12:09 pm - 8:56 pm
BOS
-
MSN
9h 47m
1 stop
$280American Airlines
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 $253 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 $253.

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 Monday and avoid Thursdays 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
Best time to beat the crowds with an average 9% drop in price.
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 $323 on average. Morning departures are around 37% 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 - $388 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 8110 reviews
7.9Comfort
7.8Entertainment
8.1Boarding
8.5Crew
7.2Food
Airline reviews

Outdated equipment in disrepair, wifi inoperable.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

2.0 MediocreGary, Jan 2026
CLE - DTW
Read more Delta reviews

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.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

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

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

No enough space plus only allowing one laggage instead of two like other airlines.

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

Information on your arrival and departure airports