$114 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 8/31. 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

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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
Boston2 stops$286
Albany
Albany1 stop$329
Boston
Boston2 stops$286
Albany
Albany1 stop$329

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

Mon, May 18 - Wed, May 27
Multiple Airlines Logo
6:50 pm - 9:12 am
MSN
-
BOS
37h 22m
2 stops
Multiple Airlines Logo
9:20 am - 5:25 pm
BOS
-
MSN
9h 05m
1 stop
$286Multiple Airlines
Sat, Sep 12 - Sat, Sep 19
Delta Logo
4:00 pm - 7:34 pm
MSN
-
BOS
2h 34mnonstop
Delta Logo
1:20 pm - 3:13 pm
BOS
-
MSN
2h 53mnonstop
$313Delta
Wed, May 6 - Sat, May 9
Multiple Airlines Logo
6:05 pm - 9:12 am
MSN
-
BOS
14h 07m
1 stop
Multiple Airlines Logo
10:07 am - 8:25 am
BOS
-
MSN
47h 18m
2 stops
$315Multiple Airlines
Mon, May 4 - Fri, May 8
American Airlines Logo
6:20 am - 2:14 pm
MSN
-
ORH
6h 54m
1 stop
American Airlines Logo
2:39 pm - 11:28 pm
ORH
-
MSN
9h 49m
1 stop
$320American Airlines
Wed, Aug 12 - Wed, Aug 19
Delta Logo
7:00 am - 3:23 pm
MSN
-
BOS
7h 23m
1 stop
Delta Logo
1:20 pm - 3:13 pm
BOS
-
MSN
2h 53mnonstop
$323Delta
Wed, Aug 12 - Wed, Aug 19
United Airlines Logo
5:00 am - 11:07 am
MSN
-
BOS
5h 07m
1 stop
United Airlines Logo
6:00 am - 9:44 am
BOS
-
MSN
4h 44m
1 stop
$328United Airlines
Sat, May 16 - Mon, May 18
Delta Logo
6:20 pm - 11:18 pm
MSN
-
ALB
3h 58m
1 stop
Delta Logo
6:06 pm - 10:44 pm
ALB
-
MSN
5h 38m
1 stop
$329Delta
Wed, May 20 - Sat, May 23
Delta Logo
6:29 pm - 11:57 pm
MSN
-
BDL
4h 28m
1 stop
Delta Logo
6:00 am - 11:08 am
BDL
-
MSN
6h 08m
1 stop
$329Delta
Sat, May 23 - Sun, May 31
American Airlines Logo
6:02 am - 4:53 pm
MSN
-
ORH
9h 51m
1 stop
American Airlines Logo
5:18 pm - 7:49 am
ORH
-
MSN
15h 31m
2 stops
$330American Airlines
Sat, May 16 - Fri, May 22
United Airlines Logo
4:02 pm - 11:59 pm
MSN
-
ALB
6h 57m
2 stops
United Airlines Logo
4:48 pm - 9:07 pm
ALB
-
MSN
5h 19m
1 stop
$334United 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.

How much is a round-trip flight from Madison to Massachusetts?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Madison to Massachusetts departing in May.

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 $313 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 $313.

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

The average price for all round-trip flights from Madison to Massachusetts depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Massachusetts is generally in the evening, when round-trip flights cost $393 on average. Morning departures are around 5% 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 $411.

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 January, when tickets cost $306 (return) on average. On the other hand, the most expensive months are March and April, when the average cost of round-trip tickets is $484 and $431 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 Tuesdays if you are looking for the best rates. For your return to Madison, you’ll find the best rates on Tuesdays and the most expensive ones on Mondays.

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 3 weeks before departure, which saves you about 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$114
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Madison to Hartford

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.

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 $251 one-way - $390 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 8434 reviews
8.1Boarding
7.9Comfort
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

4.0 OkayDerek, Apr 2026
SEA - HNL
Read more Delta reviews

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

The flight was delayed from take off because only one runway was operational in San Francisco.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Really hard landing... as in slammed into the runway then hit the brakes really hard ...

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

Returned home with a blood clot from flight homes and the uncomfortable aircraft I was on.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

Everything was delayed and the staff sent me to the wrong gate, causing me to miss one of my flights. I arrived at my destination 6 hours later than I was supposed to.

Got home at 3am after deboarding the plane. No compensation offered by American

Delayed flight. Missed connection, AA put us on a later connecting flight. The connection flight was delayed 4 times and we had to deplane. Didnt get home until 3am, when I was supposed to be home at 8:30p. Zero compensation offered from American. I would not fly them again.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

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

Information on your arrival and departure airports