HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$94+ Cheap flights from New Windsor (SWF) to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/7. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stewart to Massachusetts with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Stewart to Massachusetts

Keep the following information in mind while searching for Stewart to Massachusetts flight deals. Data was last updated June 12, 2025.

Round-trip from

$224
(Mytrip)

One-way from

$94
(Mytrip)

Popular in

April

Cheapest in

October

Average price

$215
From New Windsor Stewart to Massachusetts
Search Deals
One-way flight from New Windsor Stewart to Massachusetts
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($46 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Stewart to Massachusetts

Cheapest flights from Stewart to Massachusetts
Explore the most affordable flight options available from Stewart to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/257:56 pmSWF - BOS
1 stop23h 38mMultiple Airlines
Mon 7/286:10 amBOS - SWF
1 stop12h 56mMultiple Airlines
Deal found 6/11$224
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/106:42 pmSWF - BDL
1 stop14h 38mMultiple Airlines
Thu 7/1710:15 amBDL - SWF
1 stop7h 37mMultiple Airlines
Deal found 6/10$287
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/256:35 pmSWF - ALB
1 stop14h 15mAllegiant Air
Sun 6/292:04 pmALB - SWF
1 stop27h 17mAllegiant Air
Deal found 6/10$427
This Mytrip deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/256:35 pmSWF - ALB
1 stop14h 15mMultiple Airlines
Sun 6/292:04 pmALB - SWF
2 stops29h 07mMultiple Airlines
Deal found 6/10$487
This KAYAK deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/107:52 pmSWF - BDL
2 stops21h 49mBreeze Airways
Thu 7/178:05 amBDL - SWF
2 stops11h 07mBreeze Airways
Deal found 6/10$755

Cheapflights Fare Finder

Customize your flight search to find flights from Stewart to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from New Windsor to Massachusetts that are best for you.

Fly from

Stewart

Fly to

Massachusetts

Route

Depart

Return

Price

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 7/25

7:56 pm-7:34 pm

1 stop23h 38m

Boston Logan Intl

Mon 7/28

6:10 am-7:06 pm

1 stop12h 56m

$224

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Thu 7/10

6:42 pm-9:20 am

1 stop14h 38m

Hartford Bradley Intl

Thu 7/17

10:15 am-5:52 pm

1 stop7h 37m

$287

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 6/25

6:35 pm-8:50 am

1 stop14h 15m

Albany Intl

Sun 6/29

2:04 pm-5:21 pm

1 stop27h 17m

$427

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 6/25

6:35 pm-8:50 am

1 stop14h 15m

Albany Intl

Sun 6/29

2:04 pm-7:11 pm

2 stops29h 07m

$487

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Thu 7/10

7:52 pm-5:41 pm

2 stops21h 49m

Hartford Bradley Intl

Thu 7/17

8:05 am-7:12 pm

2 stops11h 07m

$755

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 7/7

7:56 pm-3:37 pm

1 stop19h 41m

$94

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Fri 7/11

7:56 pm-3:13 pm

1 stop19h 17m

$100

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 8/31

12:13 pm-9:49 am

2 stops21h 36m

$188

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Sun 7/20

7:52 pm-5:41 pm

2 stops21h 49m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Best time to book a flight from Stewart to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Stewart with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Massachusetts

What is the cheapest month to book a flight from New Windsor to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $218). Flying from New Windsor to Massachusetts in June is currently the most expensive (average of $306). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated June 12, 2025.
Breeze Airways
8.1
Very good
178 reviews

Overall

8.1

Entertainment

6.6

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Overall

8.1

Entertainment

6.6

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Allegiant Air
7.3
Good
725 reviews
Breeze Airways
8.1
Very good
178 reviews

Overall

8.1

Entertainment

6.6

Comfort

8.2

Food

6.7

Boarding

8.3

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Find useful and relevant information for your journey from Stewart to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Windsor to Massachusetts?

    If you book a flight to Massachusetts from New Windsor, you will be flying from Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor.

  • What are the most popular routes from New Windsor to Massachusetts?

    The most popular flight routes from New Windsor to Massachusetts are New Windsor Stewart - Boston Logan Intl, New Windsor Stewart - Hartford Bradley Intl and New Windsor Stewart - Albany Intl.

  • Can I find deals for flights from Stewart to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Stewart to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Massachusetts.

  • Can I find deals for business class flights from Stewart to Massachusetts?

    Yes. Cheapflights offers flight deals from Stewart to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Windsor to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $218). Flying from New Windsor to Massachusetts in June is currently the most expensive (average of $306). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stewart to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
John F Kennedy Intl to O'Hare Intl flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Orlando flights
Newark to Miami flights
Newark to Los Angeles flights
LaGuardia to O'Hare Intl flights
LaGuardia to Miami flights
Newark to Seattle flights
John F Kennedy Intl to Seattle flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Fort Lauderdale flights
LaGuardia to Fort Lauderdale flights
Newark to Orlando flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to San Francisco flights
Newark to O'Hare Intl flights
Newark to Las Vegas flights
John F Kennedy Intl to Atlanta flights
LaGuardia to Denver flights
Newark to Dallas/Fort Worth flights
LaGuardia to Orlando flights
Newark to San Francisco flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Denver flights
Newark to Midway flights
John F Kennedy Intl to Hobby flights
John F Kennedy Intl to West Palm Beach flights
LaGuardia to Atlanta flights
LaGuardia to Las Vegas flights
LaGuardia to Hobby flights
Newark to Denver flights
John F Kennedy Intl to Midway flights
LaGuardia to Seattle flights
Newark to Atlanta flights
John F Kennedy Intl to Honolulu flights
John F Kennedy Intl to Tampa flights
Newark to Tampa flights
Newark to Hobby flights
John F Kennedy Intl to Ontario flights
Newark to Burbank flights
LaGuardia to San Francisco flights
Newark to New Orleans flights
Newark to Santa Ana flights
John F Kennedy Intl to Nashville flights
Newark to Sky Harbor Intl flights
John F Kennedy Intl to San Diego flights
LaGuardia to Nashville flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.