When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 25 days in advance, which can save you up to 91% on flights from New Windsor to Portland compared to booking the week you need them. Waiting 25 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $408. For sooner than that we have options available in the next 3 days from $645.
Flights from New Windsor to Portland lean towards being more expensive in December. Prices are generally better when you fly from New Windsor to Portland in September, with the cheapest ticket starting at $99.
When flying from New Windsor to Portland, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$439 - $534
Route
Depart
Return
Price
New Windsor StewartPortland
SWF - PDX
SWFPDX
New Windsor Stewart
Fri 7/19
2 stops13h 57m
Portland
Tue 7/23
3 stops24h 23m
New Windsor StewartPortland
SWF - PDX
SWFPDX
New Windsor Stewart
Fri 7/19
2 stops13h 57m
Portland
Tue 7/23
3 stops24h 23m
New Windsor StewartPortland
SWF - PDX
SWFPDX
New Windsor Stewart
Fri 7/19
3 stops27h 22m
Portland
Tue 7/23
3 stops24h 23m
New Windsor StewartPortland
SWF - PDX
SWFPDX
New Windsor Stewart
Sun 6/23
2 stops21h 52m
Portland
Sun 6/30
2 stops15h 12m
New Windsor StewartPortland
SWF - PDX
SWFPDX
New Windsor Stewart
Mon 7/1
3 stops25h 22m
Portland
Thu 7/4
3 stops27h 46m
New Windsor StewartPortland
SWF - PDX
SWFPDX
New Windsor Stewart
Fri 7/19
2 stops13h 57m
Portland
Tue 7/23
2 stops24h 23m
New Windsor StewartPortland
SWF - PDX
SWFPDX
New Windsor Stewart
Fri 7/19
2 stops13h 57m
Portland
Tue 7/23
2 stops24h 23m
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