$83 Find Cheap Flights from Orlando 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 Orlando 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 Orlando 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 Orlando to Massachusetts, as well as popular online travel agencies
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Cheap Flights from Orlando to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Bostonnonstop$156
Albany
Albany1 stop$197
Boston
Bostonnonstop$156
Albany
Albany1 stop$197

Book Cheap Orlando 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 Orlando 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 Orlando to Massachusetts

Fri, Aug 28 - Mon, Aug 31
Multiple Airlines Logo
8:45 am - 11:38 am
MCO
-
BDL
2h 53mnonstop
Multiple Airlines Logo
7:11 pm - 11:41 pm
BDL
-
MCO
4h 30m
1 stop
$143Multiple Airlines
Fri, Aug 28 - Mon, Aug 31
Frontier Logo
8:45 am - 11:38 am
MCO
-
BDL
2h 53mnonstop
Frontier Logo
12:33 pm - 3:34 pm
BDL
-
MCO
3h 01mnonstop
$147Frontier
Wed, Aug 12 - Tue, Aug 18
Delta Logo
4:45 pm - 11:57 pm
MCO
-
ALB
7h 12m
1 stop
Delta Logo
9:45 am - 4:49 pm
ALB
-
MCO
7h 04m
1 stop
$197Delta
Wed, Sep 9 - Mon, Sep 14
Southwest Logo
10:20 am - 3:35 pm
MCO
-
ALB
5h 15m
1 stop
Southwest Logo
6:30 am - 9:25 am
ALB
-
MCO
2h 55mnonstop
$200Southwest
Tue, Sep 1 - Sun, Sep 6
American Airlines Logo
4:21 pm - 9:27 pm
MCO
-
ALB
5h 06m
1 stop
American Airlines Logo
4:14 pm - 10:00 pm
ALB
-
MCO
5h 46m
1 stop
$202American Airlines
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
6:50 pm - 9:40 pm
MCO
-
ALB
2h 50mnonstop
Southwest Logo
6:30 am - 9:25 am
ALB
-
MCO
2h 55mnonstop
$208Southwest
Sat, Jun 20 - Tue, Jun 23
JetBlue Logo
8:55 pm - 11:54 pm
MCO
-
ALB
2h 59mnonstop
JetBlue Logo
6:32 am - 9:39 am
ALB
-
MCO
3h 07mnonstop
$217JetBlue
Wed, Jul 8 - Tue, Jul 14
Delta Logo
10:48 am - 5:00 pm
MCO
-
ORH
6h 12m
1 stop
Delta Logo
5:40 pm - 11:03 pm
ORH
-
MCO
5h 23m
1 stop
$252Delta
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
5:46 pm - 4:51 pm
MCO
-
ORH
23h 05m
2 stops
American Airlines Logo
5:16 pm - 9:44 am
ORH
-
MCO
16h 28m
1 stop
$262American Airlines
Sat, Jun 20 - Tue, Jun 30
JetBlue Logo
8:58 am - 11:49 am
MCO
-
ORH
2h 51mnonstop
JetBlue Logo
2:35 pm - 5:43 pm
ORH
-
MCO
3h 08mnonstop
$268JetBlue
Booking Insights

KAYAK's insights & trends for Orlando to Massachusetts flights

Get data-powered insights and trends into flights from Orlando 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 Orlando Airport 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 Orlando Airport to Massachusetts departing in September.

What is the cheapest Orlando Airport to Massachusetts flight route?

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

The cheapest ticket to Massachusetts from Orlando Airport found in the last 5 days was to Worcester, at $108 round-trip. The most popular route is from Orlando Airport (MCO) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 5 days was $153.

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

The average price for all round-trip flights from Orlando Airport 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 at night, when round-trip flights cost $231 on average. Morning departures are around 61% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $784.

Can I save money by flying with a layover from Orlando Airport 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.

No, with an average price for the route of $304, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Orlando Airport to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando Airport 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 Orlando Airport to Massachusetts is December, when tickets cost $39 (return) on average. On the other hand, the most expensive months are September and November, when the average cost of round-trip tickets is $507 and $359 respectively.

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

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

If your flying dates are flexible, you should consider flying to Massachusetts on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Orlando to Massachusetts. For your return ticket, we recommend flying on a Thursday and avoiding Mondays for the best deals.

How far in advance should I book a flight from Orlando Airport 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 Orlando Airport 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 Orlando Airport to Massachusetts, you should book around 2 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$83
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Orlando Airport to Hartford

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Orlando 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 Orlando to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Orlando 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 Orlando 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 Orlando 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 Orlando 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 Orlando 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 Orlando to the following destinations at these prices or less: Boston $169 one-way - $281 round-trip

Reviews of the top 5 airlines serving from Orlando to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Orlando 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 Orlando 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.
8.0
SouthwestOverall score based on 4255 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

2.0 MediocreDawn, Jun 2026
BUF - BWI
Read more Southwest reviews

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Aside from a completely packed plane, I really have no complaints.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

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

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

It was great. Smooth flight, comfortable, left on time and landed on time.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was easy. Provided drinks and snacks. Good aircraft and staff

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

It was an early flight and most people napped/slept and the crew let us which was nice.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

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

Information on your arrival and departure airports