There are 9 ways to get from Portland to Ossining by plane, train, train (Amtrak), car, or bus
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to John F. Kennedy International Airport, train
best- Fly from Portland International Airport (PDX) to John F. Kennedy International Airport (JFK)PDX - JFK
- Take the train from Grand Central Terminal to Ossining
8h 50m$216–838Fly to Laguardia Airport, train
cheapest- Fly from Portland International Airport (PDX) to Laguardia Airport (LGA)PDX - LGA
- Take the train from 125th Street - Harlem to Ossining
10h 28m$205–826Train (Amtrak)
- Take the train from Portland to Chicago Union Station
- Take the train from Chicago Union Station to Croton-Harmon Amtrak Station
2d 18h$423–1,950Drive 2,898.5 mi
- Drive from Portland to Ossining2,898.5 mi
46h 16m$529–765Fly to Newark Liberty International Airport, train
- Fly from Portland International Airport (PDX) to Newark Liberty International Airport (EWR)PDX - EWR
- Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Station
9h 21m$298–646Fly to Westchester County Airport
- Fly from Portland International Airport (PDX) to Westchester County Airport (HPN)PDX - HPN
11h 58m$309–1,309Fly to Long Island Mac Arthur Airport, train
- Fly from Portland International Airport (PDX) to Long Island Mac Arthur Airport (ISP)PDX - ISP
- Take the train from Central Islip to Jamaica
- Take the train from Grand Central Terminal to Ossining
13h 28m$347–1,351Fly to Philadelphia International Airport, train
- Fly from Portland International Airport (PDX) to Philadelphia International Airport (PHL)PDX - PHL
- Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Station
- Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Station
10h 52m$320–1,118Bus, train
- Take the bus from Portland Curbside Bus Stop to Vancouver
- Take the train from Vancouver to Toronto Union Station
- Take the train from Toronto Union Station to Croton-Harmon
4d 19h$365–664
Portland to Ossining by train (Amtrak)
Questions & Answers
The cheapest way to get from Portland to Ossining is to fly and train which costs $200 - $850 and takes 10h 28m.
The fastest way to get from Portland to Ossining is to fly and train which takes 8h 50m and costs $210 - $850.
No, there is no direct train from Portland to Ossining. However, there are services departing from Portland and arriving at Ossining via Chicago Union Station and Croton-Harmon. The journey, including transfers, takes approximately 2 days 18h.
The distance between Portland and Ossining is 2519 miles. The road distance is 2915.5 miles.
The best way to get from Portland to Ossining without a car is to train which takes 2 days 18h and costs $420 - $2,000.
It takes approximately 8h 50m to get from Portland to Ossining, including transfers.
Portland to Ossining train services, operated by Amtrak, depart from Portland station.
The best way to get from Portland to Ossining is to train which takes 2 days 18h and costs $420 - $2,000. Alternatively, you can fly, which costs $300 - $1,400 and takes 11h 58m.
Ossining is 3h ahead of Portland. It is currently 10:59 PM in Portland and 1:59 AM in Ossining.
Portland to Ossining train services, operated by Amtrak, arrive at Chicago Union Station.
What companies run services between Portland, OR, USA and Ossining, NY, USA?
You can take a train from Portland to Ossining via Chicago Union Station and Croton-Harmon in around 2d 18h. Alternatively, Alaska Airlines, Inc., American Airlines, and Delta fly from Portland International Airport (PDX) to Westchester County Airport (HPN) every 4 hours.
Transport is disrupted due to the Russia-Ukraine war. Read more
- Website
- delta.com
Flights from Portland International Airport to John F. Kennedy International Airport
- Ave. Duration
- 5h 21m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to John F. Kennedy International Airport via Minneapolis
- Ave. Duration
- 7h 46m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to John F. Kennedy International Airport via Detroit
- Ave. Duration
- 9h 44m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to Laguardia Airport via Minneapolis
- Ave. Duration
- 7h 56m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to Laguardia Airport via Detroit
- Ave. Duration
- 9h 50m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to Newark Liberty International Airport via Minneapolis
- Ave. Duration
- 8h 16m
- When
- Every day
- Estimated price
- $170–750
Flights from Portland International Airport to Newark Liberty International Airport via Detroit
- Ave. Duration
- 9h 49m
- When
- Every day
- Estimated price
- $170–750
Flights from Portland International Airport to Westchester County Airport via Minneapolis
- Ave. Duration
- 7h 34m
- When
- Every day
- Estimated price
- $300–1,300
Flights from Portland International Airport to Westchester County Airport via Atlanta
- Ave. Duration
- 8h 44m
- When
- Every day
- Estimated price
- $350–1,400
Flights from Portland International Airport to Westchester County Airport via Detroit
- Ave. Duration
- 9h 44m
- When
- Friday to Sunday
- Estimated price
- $300–1,300
Flights from Portland International Airport to Philadelphia International Airport via Minneapolis
- Ave. Duration
- 7h 35m
- When
- Every day
- Estimated price
- $220–900
Flights from Portland International Airport to Philadelphia International Airport via Detroit
- Ave. Duration
- 9h 22m
- When
- Every day
- Estimated price
- $220–900
- Website
- united.com
Flights from Portland International Airport to Laguardia Airport via Chicago O'Hare
- Ave. Duration
- 7h 10m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to Laguardia Airport via Washington Dulles
- Ave. Duration
- 7h 24m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to Newark Liberty International Airport
- Ave. Duration
- 5h 1m
- When
- Every day
- Estimated price
- $170–750
Flights from Portland International Airport to Newark Liberty International Airport via Chicago O'Hare
- Ave. Duration
- 7h 34m
- When
- Every day
- Estimated price
- $170–750
Flights from Portland International Airport to Newark Liberty International Airport via Washington Dulles
- Ave. Duration
- 7h 36m
- When
- Monday
- Estimated price
- $180–750
Flights from Portland International Airport to Philadelphia International Airport via Chicago O'Hare
- Ave. Duration
- 7h 24m
- When
- Every day
- Estimated price
- $220–950
Flights from Portland International Airport to Philadelphia International Airport via Washington Dulles
- Ave. Duration
- 7h 45m
- When
- Monday, Tuesday, Wednesday, Friday, and Sunday
- Estimated price
- $220–950
- Website
- alaskaair.com
Flights from Portland International Airport to John F. Kennedy International Airport
- Ave. Duration
- 5h 21m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to Laguardia Airport via Chicago O'Hare
- Ave. Duration
- 7h 40m
- When
- Monday, Tuesday, Friday, and Sunday
- Estimated price
- $190–800
Flights from Portland International Airport to Laguardia Airport via Reagan Washington
- Ave. Duration
- 8h 47m
- When
- Every day
- Estimated price
- $190–800
Flights from Portland International Airport to Newark Liberty International Airport
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $170–750
Flights from Portland International Airport to Westchester County Airport via Chicago O'Hare
- Ave. Duration
- 8h 27m
- When
- Every day
- Estimated price
- $300–1,300
Flights from Portland International Airport to Westchester County Airport via Reagan Washington
- Ave. Duration
- 9h 4m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $310–1,300
Flights from Portland International Airport to Philadelphia International Airport
- Ave. Duration
- 5h 6m
- When
- Every day
- Estimated price
- $220–900
- Website
- southwest.com
Flights from Portland International Airport to Laguardia Airport via Chicago Midway
- Ave. Duration
- 7h 50m
- When
- Monday, Tuesday, Wednesday, and Saturday
- Estimated price
- $190–800
Flights from Portland International Airport to Laguardia Airport via St. Louis
- Ave. Duration
- 9h 55m
- When
- Saturday
- Estimated price
- $200–800
Flights from Portland International Airport to Long Island Mac Arthur Airport via Baltimore
- Ave. Duration
- 11h 30m
- When
- Friday and Saturday
- Estimated price
- $320–1,300
Flights from Portland International Airport to Long Island Mac Arthur Airport via Orlando
- Ave. Duration
- 10h 44m
- When
- Monday
- Estimated price
- $420–1,700
Flights from Portland International Airport to Long Island Mac Arthur Airport via Chicago Midway, Baltimore
- Ave. Duration
- 13h 45m
- When
- Saturday
- Estimated price
- $320–1,300
Flights from Portland International Airport to Philadelphia International Airport via Chicago Midway
- Ave. Duration
- 6h 40m
- When
- Friday and Sunday
- Estimated price
- $220–950
Flights from Portland International Airport to Philadelphia International Airport via St. Louis
- Ave. Duration
- 9h 30m
- When
- Saturday
- Estimated price
- $230–950
- Website
- aa.com
Flights from Portland International Airport to Laguardia Airport via Chicago O'Hare
- Ave. Duration
- 7h 23m
- When
- Monday, Tuesday, Wednesday, Friday, and Sunday
- Estimated price
- $190–800
Flights from Portland International Airport to Newark Liberty International Airport via Chicago O'Hare
- Ave. Duration
- 7h 53m
- When
- Every day
- Estimated price
- $170–750
Flights from Portland International Airport to Westchester County Airport via Charlotte
- Ave. Duration
- 8h 14m
- When
- Every day
- Estimated price
- $340–1,400
Flights from Portland International Airport to Westchester County Airport via Chicago O'Hare
- Ave. Duration
- 8h 52m
- When
- Every day
- Estimated price
- $300–1,300
Flights from Portland International Airport to Philadelphia International Airport
- Ave. Duration
- 4h 59m
- When
- Thursday to Sunday
- Estimated price
- $220–900
Flights from Portland International Airport to Philadelphia International Airport via Chicago O'Hare
- Ave. Duration
- 9h 10m
- When
- Monday, Tuesday, Friday, Saturday, and Sunday
- Estimated price
- $220–950
- Website
- capeair.com
Flights from Portland International Airport to Long Island Mac Arthur Airport via Boston
- Ave. Duration
- 9h 2m
- When
- Every day
- Estimated price
- $330–1,400
- Website
- flyfrontier.com
Flights from Portland International Airport to Long Island Mac Arthur Airport via Orlando
- Ave. Duration
- 9h 28m
- When
- Tuesday, Wednesday, and Friday
- Estimated price
- $420–1,700
- Phone
- 877.690.5114
- Website
- mta.info
Train from Grand Central Terminal to Ossining
- Ave. Duration
- 1h 3m
- Frequency
- Every 30 minutes
- Estimated price
- $10–17
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $10–12
- Peak
- $14–17
Train from 125th Street - Harlem to Ossining
- Ave. Duration
- 52 min
- Frequency
- Every 30 minutes
- Estimated price
- $10–16
- Website
- https://www.mta.info/agency/metro-north-railroad
- Schedules at
- https://www.mta.info/schedules
- Off-Peak
- $10–11
- Peak
- $13–16
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Portland to Chicago Union Station
- Ave. Duration
- 46h
- Frequency
- Twice daily
- Estimated price
- $300–1,300
- Website
- https://www.amtrak.com/home.html
Train from Chicago Union Station to Croton-Harmon Amtrak Station
- Ave. Duration
- 19h 23m
- Frequency
- Once daily
- Estimated price
- $110–700
- Website
- https://www.amtrak.com/home.html
Train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Station
- Ave. Duration
- 43 min
- Frequency
- Every 2 hours
- Estimated price
- $19–55
- Website
- https://www.amtrak.com/home.html
Train from 30th Street Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 1h 24m
- Frequency
- Hourly
- Estimated price
- $28–340
- Website
- https://www.amtrak.com/home.html
- Phone
- +1-718-217-5477
- Website
- mta.info
Train from Central Islip to Jamaica
- Ave. Duration
- 50 min
- Frequency
- Every 30 minutes
- Estimated price
- $9–22
- Website
- https://www.mta.info/agency/long-island-rail-road
- Schedules at
- https://www.mta.info/agency/long-island-rail-road/timetables
- Off-Peak
- $9–14
- Peak
- $13–22
Rome2Rio's guide to Amtrak Northeast Regional
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from 30th Street Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 1h 26m
- Frequency
- Hourly
- Estimated price
- $12–230
- Website
- https://www.amtrak.com/home.html
- Schedules at
- https://www.amtrak.com/northeast-regional-train
- Coach
- $12–230
- Business Class
- $60–270
Rome2Rio's guide to Amtrak Acela
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from 30th Street Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 1h 20m
- Frequency
- Every 2 hours
- Estimated price
- $20–600
- Schedules at
- https://www.amtrak.com/acela-train
- Website
- https://www.amtrak.com/home.html
- Business Class
- $20–460
- First Class
- $130–600
- Phone
- +1 888 842-7245
- Website
- viarail.ca
Train from Vancouver to Toronto Union Station
- Ave. Duration
- 3d 20h
- Frequency
- Twice a week
- Estimated price
- $250–450
- Website
- https://www.viarail.ca/en
- Economy Adult - same day booking
- $250–450
- Economy Adult - Advanced Booking
- $350–450
- Economy Escape Advanced Booking - Adult
- $330–390
Train from Toronto Union Station to Croton-Harmon
- Ave. Duration
- 12h 59m
- Frequency
- Once daily
- Estimated price
- $70–130
- Website
- https://www.viarail.ca/en
- Economy Adult - same day booking
- $85–130
- Economy Adult - Advanced Booking
- $85–110
- Economy Escape Advanced Booking - Adult
- $70–90
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Portland Curbside Bus Stop to Vancouver
- Ave. Duration
- 7h 50m
- Frequency
- 5 times a week
- Estimated price
- $35–75
- Schedules at
- flixbus.com
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More Questions & Answers
Yes, the driving distance between Portland to Ossining is 2915 miles. It takes approximately 46h 16m to drive from Portland to Ossining.
There are 106+ hotels available in Ossining.




















