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Find cheap flights from Stewart Intl. to Massachusetts from $82

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Windsor to Massachusetts departing on 5/20. 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
0 bags
Sun 6/2
Sun 6/9

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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$391

Good to know

Cheapest flight

$82
Flight from New Windsor to Boston

FAQs - booking Massachusetts flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Massachusetts from Stewart Intl. 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 Stewart Intl. 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 Stewart Intl. with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Stewart Intl. 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 Stewart Intl. 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

  • Morning departure is around 69% 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 airlines flying from New Windsor to Massachusetts

 
Need help choosing which airline to fly with from New Windsor 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 4552 reviews
7.8Boarding
8.3Crew
7.9Comfort
7.5Entertainment
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

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

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.

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

There were weather issues and coding problems whatever those refer to, but JetBlue, for two days in a row was unbelievably late. Several hours late, resulting in almost no sleep for passengers like me.

The plane was very hot. There were delays . Generally, the flight was great.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

Overall it was a good experience. Stewards were very kind and professional. The departure and arrival times were as promised. Plane was clean.

No frills, limited comfort, no food, no entertainment, but fine

The seat was very uncomfortable from Boston to Nashville. Otherwise the flight was excellent.

Seats horrible. No way of getting comfortable . But flight ran smoothly

I had a phobia for Spirit and now is 100% confirmed. Flight delayed, missed connecting flight and staying overnight . Now not even able to get my boarding pass until I’ll get into the airport. It’s really really bad at this point

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

the landing was terrible. the plane touched down and had take off. the plane flew around and landed a second time.i understand the weather might of been the problem. It was a scary experience and no explanation from the captain.

Pack light and enjoy the quick boarding and early departure and arrivals.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Book cheap flights from Stewart Intl. to Massachusetts

Recent round-trip flight deals

5/10Fri
1 stop
11h 36mSWF-BOS
5/12Sun
1 stop
11h 39mBOS-SWF
$391
5/9Thu
2 stops
13h 30mSWF-BOS
5/16Thu
3 stops
30h 06mBOS-SWF
$592
5/9Thu
1 stop
9h 44mSWF-BOS
5/16Thu
3 stops
30h 06mBOS-SWF
$604
5/9Thu
1 stop
9h 44mSWF-BOS
5/16Thu
2 stops
19h 16mBOS-SWF
$639
6/1Sat
1 stop
22h 45mSWF-BOS
6/8Sat
2 stops
21h 49mBOS-SWF
$642
5/9Thu
3 stops
35h 11mSWF-BOS
5/16Thu
3 stops
30h 06mBOS-SWF
$646
6/1Sat
1 stop
22h 45mSWF-BOS
6/8Sat
1 stop
12h 28mBOS-SWF
$651
6/1Sat
1 stop
22h 45mSWF-BOS
6/7Fri
1 stop
6h 37mBOS-SWF
$655
6/1Sat
1 stopPLAY
22h 45mSWF-BOS
6/6Thu
1 stopPLAY
22h 50mBOS-SWF
$740
6/1Sat
1 stopPLAY
22h 45mSWF-BOS
6/6Thu
1 stopPLAY
22h 50mBOS-SWF
$810

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Recent one-way flight deals

5/20Mon
1 stop
11h 36mSWF-BOS
$82
6/10Mon
1 stop
27h 57mSWF-BOS
$99
5/31Fri
1 stop
11h 36mSWF-BOS
$114
5/31Fri
1 stop
11h 36mSWF-BOS
$121
5/13Mon
1 stop
11h 36mSWF-BOS
$127
5/27Mon
1 stop
11h 36mSWF-BOS
$133
7/22Mon
1 stop
27h 42mSWF-BOS
$150
6/2Sun
1 stop
9h 44mSWF-BOS
$151
5/10Fri
1 stop
11h 36mSWF-BOS
$166
5/24Fri
1 stop
11h 36mSWF-BOS
$168

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Last minute flights from New Windsor to Massachusetts

Last minute flight, train and bus deals

5/8Wed
multi-stopPLAY
22h 45mSWF-BOS
5/12Sun
multi-stopPLAY
22h 50mBOS-SWF
$854
5/4Sat
multi-stopPLAY
22h 45mSWF-BOS
5/7Tue
multi-stopPLAY
22h 50mBOS-SWF
$870
5/8Wed
multi-stopPLAY
22h 45mSWF-BOS
5/14Tue
multi-stopPLAY
22h 50mBOS-SWF
$952
5/6Mon
multi-stopPLAY
22h 45mSWF-BOS
5/9Thu
multi-stopPLAY
22h 50mBOS-SWF
$998

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New Windsor - Massachusetts Flights

Departure:

Stewart Intl. (SWF)United States

Return flight deals:

Massachusetts - Stewart Intl.

Cabin classes: