$124 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 5/18. 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$266
Albany
Albany1 stop$269
Boston
Boston1 stop$266
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

Tue, Apr 28 - Fri, May 1
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
$260American Airlines
Wed, May 6 - Sat, May 9
American Airlines Logo
5:30 am - 2:26 pm
MSN
-
BOS
7h 56m
1 stop
American Airlines Logo
6:30 am - 2:31 pm
BOS
-
MSN
9h 01m
1 stop
$266American Airlines
Tue, May 12 - Mon, May 18
Delta Logo
6:19 pm - 11:18 pm
MSN
-
ALB
3h 59m
1 stop
Delta Logo
2:12 pm - 8:12 pm
ALB
-
MSN
7h 00m
1 stop
$269Delta
Tue, May 12 - Tue, May 19
Delta Logo
6:19 pm - 11:35 pm
MSN
-
BDL
4h 16m
1 stop
Delta Logo
6:00 am - 10:16 am
BDL
-
MSN
5h 16m
1 stop
$269Delta
Thu, Apr 16 - Sun, Apr 26
American Airlines Logo
6:20 am - 2:14 pm
MSN
-
ORH
6h 54m
1 stop
American Airlines Logo
2:39 pm - 11:05 am
ORH
-
MSN
21h 26m
2 stops
$270American Airlines
Wed, May 27 - Wed, Jun 3
United Airlines Logo
10:40 am - 11:47 pm
MSN
-
ALB
12h 07m
2 stops
United Airlines Logo
6:46 pm - 10:50 pm
ALB
-
MSN
5h 04m
1 stop
$274United Airlines
Wed, May 13 - Sun, May 17
Multiple Airlines Logo
6:05 pm - 7:17 pm
MSN
-
BDL
24h 12m
1 stop
Multiple Airlines Logo
1:07 pm - 8:25 am
BDL
-
MSN
20h 18m
2 stops
$278Multiple Airlines
Sat, Mar 14 - Wed, Mar 18
United Airlines Logo
6:30 am - 2:15 pm
MSN
-
BDL
6h 45m
1 stop
United Airlines Logo
6:00 am - 11:38 am
BDL
-
MSN
6h 38m
1 stop
$279United Airlines
Fri, May 15 - Thu, May 21
Breeze Airways Logo
6:50 pm - 6:52 pm
MSN
-
BDL
23h 02m
1 stop
Breeze Airways Logo
6:20 am - 8:25 am
BDL
-
MSN
27h 05m
1 stop
$331Breeze Airways
Wed, May 13 - Thu, May 21
Multiple Airlines Logo
6:05 pm - 7:17 pm
MSN
-
BDL
24h 12m
1 stop
Multiple Airlines Logo
6:20 am - 8:25 am
BDL
-
MSN
27h 05m
1 stop
$342Multiple 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 $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 January, when tickets cost $306 (return) on average. On the other hand, the most expensive months are February and March, when the average cost of round-trip tickets is $495 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 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 24% 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$124
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 18% 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 $379 on average. Morning departures are around 3% 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 $391.

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 $198 one-way - $326 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 8245 reviews
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
7.9Comfort
Airline reviews

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

10.0 ExcellentGrace, Feb 2026
JFK - LAX
Read more Delta reviews

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Everything was great except for the boarding process. Everyone is lining up all at the same time and it’s hard to tell between the groups as they are way too large.

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

It was good experience this time. The flight was on time.

I very rarely fly American and my experience today reenforces that is the correct decision. While the staff were all very courteous, our flight was first thing in the morning so there was no reason to be delayed, yet appropriate maintenance checks weren’t completed prior to our flight so we were delayed multiple times. Not a great showing, American Airlines.

It's very confusing because Kayak has it as American Airlines, but it was Hawaiian Airlines, but operated by Alaska Airlines. I had to go to the airport for my boarding pass because American said I didn't have any trips.

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

Small plane, poor meal choices for first class, bad terminal and boarding experience at LAX

Lack of gluten free options in food service. I have Celiac disease and it appears you no longer offer special meals for people with dietary restrictions. I am a frequent flyer traveling into and out of Omaha airport. I have noticed over the course of several months that although our flight typically arrives ahead of schedule (awesome job AA!) - we typically sit on the runway for several minutes waiting for the ground crew to get in place. Not sure if it is a ground crew issue or a gate availability issue (due to construction at this airport). Seems to be more of a ground crew being on time issue.

Arrived early picked up my bag in a few minutes- great trip - thank you

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

Information on your arrival and departure airports