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Find cheap flights from Orlando to Massachusetts from $29

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 6/12. 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
0 bags
Tue 6/4
Tue 6/11

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Best Massachusetts Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston1 stop$79
West Tisbury
West Tisbury1 stop$318
Albany
Albany1 stop$196

Good to know

Low season

January

High season

October

Cheapest flight

$29
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from Orlando Airport to Boston

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 to Massachusetts from Orlando 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 to Massachusetts with an airline and back to Orlando 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 to Massachusetts from Orlando up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 $109 one-way - $129 round-trip
  • Morning departure is around 18% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Orlando to Massachusetts

 
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.
7.6
JetBlueOverall score based on 4544 reviews
8.3Crew
7.5Entertainment
7.9Comfort
7.8Boarding
7.2Food
Airline reviews

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

10.0 ExcellentLeandro, Apr 2024FLL - BOS
Read more about JetBlue reviews

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Everything was good except for deplaning in NY. Took way too long!!

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

The free wi-fi was great. But, the flight delay was not sustainable. It definitely impacted people schedules and JetBlue didn’t do anything to compensate clients for it

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

I actually missed my first scheduled flight and caught it the next day. I think the check in procedure was mishandled by the baggage handler but the staff were very accommodating.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

Crew was great and did their best to make us comfortable and captain came out at the beginning to announce why the flight was delayed, weather situation up ahead, and kept us updated throughout the flight.

That flight was smooth, and staff we courteous. it was a full flight so very tight. The boarding through security was not properly controlled. it was rushed and the scanning process for our bags, etc. was pilling up at the other end with no time to empty our belonging my personal items almost toppled over on the floor if i hadn't caught it rapidly. Was it just that time, or always like this - cant say. other than that all else was fine.

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

It was terrible because the flight was delayed for 3 hours.

Flight canceled due to weather. Rescheduled flight canceled due to maintenance. I’m stuck!

Crowded flight, but upbeat and kind crew. Pilot greeted us at door, flight attendant thanked a number of “special” passengers for their business, another addressed an eight-year old boy as “young man.” United obviously trying to up their game, but though all of that is nice and notable, flying still feels like moving along a human assembly line, being herded into one small space after another (boarding areas with too few seats, planes with limited personal space, shuttles (IAD) packed too full.

You could have been ON TIME! And I was miffed because I spent an extra $82 to get my seat and the steward put a woman from the back in my aisle for nothing because her movies wouldn’t work. I’ll try that next time and save $82!

Again a nearly five hour flight and pretzels is all the food you get and all you can drink water. No electric plugs in economy. Staff was totally not caring. Delta next time

Did not like the seat spacing. The seat was very narrow and tight.

United domestic flight was better than international flight. There was no switch to control Ac In international united flight. Food was also average, Air canada food was much better than united.

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

The Flight attendant had an attitude and didn't allow anyone any time to prepare for landing despite being absent throughout the entire trip

Horrible people at the gate, they force me to check in my carry on, even thought no one behind me has to do it. I had to get out of the airport in NY to get my bag and go thru security again on my way to Honk Kong. The worst part is the employee threatened me with loosing the flights if don’t comply.

Delayed abs delayed Gate crew giving poor info - we are definitely leaving at —- Ultimately to cancel flight after 4+ hours of delays Just cancel it earlier

Delayed flight, few announcements with information, no comps, cluster f boarding because zones weren’t spread out and announced loud and repeatedly, staff did their job -nothing more nothing less, annoying kids were speaking and kicking the heck out of the back of my seat and parents weren’t willing to parent… so another typical day of air travel in the US.,

Flight was delayed until Next day as crew timed out

Nice clean modern plane no issues with the b flight

Always getting updates by email very easy to check in on line. There was plenty of checking in staff to get you all through. It was nice that the flight attendants took time to talk to you and were interested in your holiday.

This plane is my favorite despite the very limited overhead space. Seats are comfortable!

3.5 hour delay!!! No plane for hours, mechanical issues and poor communication from airline. Horrible! Supposed to land at 8:54, landed at 12:32!

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Seats suck, not enough room, overcrowded planes, hectic situation all together.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Flight was canceled. Knew there was weather, and were notified of 20 min delayed, and then suddenly canceled. Next reschedule was for 2 days. No help other than to refund. Thankfully full refund and appreciate that. I appreciate discounted airline but felt they could've done more for customer inconvenience.

Flying on Spirit Airline is a penny-pinching beat down.

Bag self drop off was terrible! No staff there to help. Almost missed my flight. Would never check a bag in with Spirit again.

Desk staff at gate were helpful. Didn't have a plane until after scheduled departure time - no explanation offered while we waited. Seats are uncomfortable - arm rests are metal and uncomfortable in a narrow seat. No food, drinks or entertainment unless purchased. They charge a huge price for carryon luggage. Flight was good.

Retired military should be able to board with Active duty like Alligint airlines does

Check in easy, price very good, no frills flying tho! Pay for Every item once seat is paid for so do the math with baggage fees and carry on fees.

They changed our gate 30 minutes before boarding began. We noticed about 20 people missed their flight due to doors closing early.

Crew members are very rude and not cooperate with passengers.

They lost my baggage on my connection flight, it’s been 24 hours since I put my claim in and still no update on my bags.

The flight was canceled, then delayed twice, we were moved gates twice. Short staff at the counter and check in. We waited for our flight 9 hours. Will never use Frontier ever again, or Spirit.

Good - Leg spar, cleanliness, and on time performance. Bad - No snacks and entertainment.

The plane was on time. Boarding went fast. Smooth flight and landing. I filled out info for a frontier credit card on the flight from Indy to Orlando and have have heard nothing back. I was supposed to get all these “instant” rewards and have received nothing g.

The only thing that may be concerning to others is the multiple notifications of a delayed flight. Then, with less than an hour before boarding, the flight was on time. The gate changed several times, leading to confusion.

The flights were right on time. The issue that was the most difficult was the lack of legroom on the planes

There was only room for a quarter of the passengers to sit at the gate at MCO. The gate attendant allowed people who did not require assistance to board early before they realized and started to turn people back. The flight was extremely uncomfortable due to pressure. My ears, eyes, sinuses and joints were very painful the whole flight. My sister also complained about her ears and sinuses as well as joints and while deplaning I heard several other passengers complain about the same issues. I’ve never felt that much discomfort flying before and I’ve been doing it for over 40 years.

Delayed over 2 hours on the way there, and back, no free drinks, no free water, no Wifi, bathroom dirty!

Even though my personal item fit into the testing compartment they had, the agent charged me for the bag and threatened to not let me board if I didn’t pay. He was doing this with everyone that was boarding, everyone was so pises. Never flying Frontier again

Book cheap flights from Orlando to Massachusetts

Recent round-trip flight deals

5/22Wed
1 stopSpirit Airlines
14h 21mMCO-BOS
5/29Wed
1 stopSpirit Airlines
6h 53mBOS-MCO
$79
5/29Wed
nonstop
3h 06mMCO-BOS
6/3Mon
1 stop
13h 00mBOS-MCO
$80
5/15Wed
nonstopFrontier
3h 16mMCO-BOS
5/18Sat
nonstopFrontier
3h 20mBOS-MCO
$99
5/29Wed
nonstopFrontier
3h 06mMCO-BOS
6/1Sat
nonstopFrontier
3h 11mBOS-MCO
$100
5/31Fri
nonstopJetBlue
2h 50mMCO-ORH
6/5Wed
nonstopJetBlue
3h 15mORH-MCO
$162
6/3Mon
nonstopJetBlue
2h 50mMCO-ORH
6/10Mon
nonstopJetBlue
3h 14mORH-MCO
$172
6/3Mon
2 stopsAmerican Airlines
22h 26mMCO-ORH
6/10Mon
2 stopsAmerican Airlines
23h 23mORH-MCO
$175
5/23Thu
2 stopsAmerican Airlines
20h 39mMCO-ORH
5/26Sun
2 stopsAmerican Airlines
22h 36mORH-MCO
$176
5/23Thu
1 stopDelta
7h 01mMCO-ORH
5/26Sun
1 stopDelta
8h 05mORH-MCO
$191
6/3Mon
1 stopDelta
7h 01mMCO-ORH
6/10Mon
1 stopDelta
5h 13mORH-MCO
$211

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Recent one-way flight deals

6/12Wed
nonstopFrontier
3h 06mMCO-BOS
$29
6/5Wed
nonstopFrontier
3h 06mMCO-BOS
$30
5/21Tue
1 stopSpirit Airlines
9h 02mMCO-BOS
$34
5/21Tue
1 stopSpirit Airlines
9h 02mMCO-BOS
$35
6/14Fri
nonstopJetBlue
2h 55mMCO-ORH
$84
5/20Mon
2 stopsAmerican Airlines
20h 28mMCO-ORH
$95
9/16Mon
1 stopAmerican Airlines
4h 29mMCO-BOS
$97
10/24Thu
nonstopJetBlue
2h 43mMCO-ORH
$109
10/10Thu
1 stopUnited Airlines
7h 23mMCO-BOS
$138
9/15Sun
2 stopsUnited Airlines
18h 11mMCO-BOS
$223

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Last minute flights from Orlando to Massachusetts

Last minute flight, train and bus deals

5/10Fri
multi-stopSpirit Airlines
22h 55mMCO-BOS
5/13Mon
multi-stopSpirit Airlines
13h 00mBOS-MCO
$118
5/10Fri
multi-stopSpirit Airlines
22h 55mMCO-BOS
5/14Tue
multi-stopSpirit Airlines
14h 29mBOS-MCO
$119
5/9Thu
nonstopFrontier
3h 07mMCO-BOS
5/14Tue
nonstopFrontier
3h 31mBOS-MCO
$135
5/9Thu
nonstopFrontier
3h 07mMCO-BOS
5/13Mon
multi-stopFrontier
16h 23mBOS-MCO
$146
5/10Fri
nonstopJetBlue
2h 50mMCO-ORH
5/12Sun
nonstopJetBlue
3h 11mORH-MCO
$298
5/10Fri
multi-stopDelta
6h 41mMCO-ORH
5/12Sun
multi-stopDelta
8h 05mORH-MCO
$311
5/6Mon
multi-stopAmerican Airlines
5h 16mMCO-BOS
5/7Tue
multi-stopAmerican Airlines
5h 51mBOS-MCO
$314
5/9Thu
multi-stopAmerican Airlines
21h 04mMCO-ORH
5/12Sun
multi-stopAmerican Airlines
18h 03mORH-MCO
$349
5/9Thu
nonstopJetBlue
2h 50mMCO-ORH
5/12Sun
nonstopJetBlue
3h 11mORH-MCO
$414
5/10Fri
multi-stopDelta
6h 41mMCO-ORH
5/12Sun
multi-stopDelta
8h 54mORH-MCO
$845

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Orlando - Massachusetts Flights