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How to get fromPortland to Westportby plane, train (Amtrak), bus (Flixbus, Greyhound), car, or train

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There are 8 ways to get from Portland to Westport by plane, train (Amtrak), bus (Flixbus, Greyhound), car, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly to Westchester County Airport

    best
    1. Fly from Portland International Airport (PDX) to Westchester County Airport (HPN)plane plane PDX - HPN
    9h 31m
    $248–838

  2. Fly to Laguardia Airport, train

    cheapest
    1. Fly from Portland International Airport (PDX) to Laguardia Airport (LGA)plane plane PDX - LGA
    2. Take the train from 125th Street - Harlem to Darientrain train
    11h 29m
    $210–884

  3. Train via Chicago

    1. Take the train from Portland to Chicago Union Stationtrain train
    2. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    3. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    4. Take the train from 125th Street - Harlem to Westporttrain train
    2d 20h
    $822–1,882

  4. Bus

    1. Take the bus from Portland Curbside Bus Stop to Pasco Bus Stopbus bus
    2. Take the bus from Pasco Bus Stop to Denver Union Stationbus bus
    3. Take the bus from Denver Union Station to Chicago Bus Stationbus bus
    4. Take the bus from Chicago Bus Station to New York Midtownbus bus
    5. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus
    3d 2h
    $523–835

  5. Drive  2,918.7 mi

    1. Drive from Portland to Westportcar car 2,918.7 mi
    46h 57m
    $533–770

  6. Fly to John F. Kennedy International Airport, train

    1. Fly from Portland International Airport (PDX) to John F. Kennedy International Airport (JFK)plane plane PDX - JFK
    2. Take the train from Grand Central Terminal to Darientrain train
    10h 14m
    $242–595

  7. Fly to Newark Liberty International Airport, train

    1. Fly from Portland International Airport (PDX) to Newark Liberty International Airport (EWR)plane plane PDX - EWR
    2. Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain train
    10h 50m
    $222–700

  8. Train

    1. Take the train from Portland to Vancouvertrain train
    2. Take the train from Vancouver to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Yonkerstrain train
    4d 22h
    $989–2,091

Portland to Westport by bus and foot

Calendar7Weekly Services
Duration3d 2hAverage Duration
Ticket$523Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Portland to Westport.ExpandLaunch map view
  • Distance: 2,471.4 mi
  • Duration: 9h 31m

What companies run services between Portland, OR, USA and Westport, CT, USA?

Alaska Airlines, Inc., American Airlines, and Delta fly from Portland International Airport (PDX) to Westchester County Airport (HPN) every 4 hours. Alternatively, you can take a train from Portland to Westport via Chicago Union Station, Croton-Harmon, 125th Street - Harlem, and Westport in around 2d 20h.

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