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

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There are 10 ways to get from Portland to Chester by plane, bus, train, bus (Flixbus, Greyhound), car, or train (Amtrak)

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 Bradley International Airport, bus

    best
    1. Fly from Portland International Airport (PDX) to Bradley International Airport (BDL)plane plane PDX - BDL
    2. Take the bus from Central Row South Side @ Travelers to Chester Park & Ride @ W Main Stbus bus
    10h 57m
    $175–713

  2. Fly to Theodore Francis Green State Airport, train

    cheapest
    1. Fly from Portland International Airport (PDX) to Theodore Francis Green State Airport (PVD)plane plane PDX - PVD
    2. Take the train from Providence to Old Saybrook Amtrak Stationtrain train
    13h 21m
    $148–565

  3. Train, bus

    1. Take the train from Portland to Chicago Union Stationtrain train
    2. Take the train from Chicago Union Station to Springfieldtrain train
    3. Take the train from Springfield to Hartford Amtrak Stationtrain train
    4. Take the bus from Asylum St @ Bushnell Park to Chester Park & Ride @ W Main Stbus bus
    2d 21h
    $959–2,054

  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 St Louis Bus Stationbus bus
    4. Take the bus from St Louis Bus Station to Port Authority Bus Terminalbus bus
    5. Take the bus from New York to Hartfordbus bus
    6. Take the bus from Asylum St @ Bushnell Park to Chester Park & Ride @ W Main Stbus bus
    3d 4h
    $497–997

  5. Drive 2,975.8 mi

    1. Drive from Portland to Chestercar car 2,975.8 mi
    2d
    $544–785

  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 Ny Moynihan Train Hall At Penn Station to Old Saybrook Amtrak Stationtrain train
    11h 52m
    $257–642

  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 Old Saybrook Amtrak Stationtrain train
    12h 10m
    $238–833

  8. Fly to Boston Logan Airport, train

    1. Fly from Portland International Airport (PDX) to Boston Logan Airport (BOS)plane plane PDX - BOS
    2. Take the train from Boston to Old Saybrook Amtrak Stationtrain train
    11h 24m
    $257–582

  9. Train (Amtrak)

    1. Take the train from Portland to Chicago Union Stationtrain train
    2. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Old Saybrook Amtrak Stationtrain train
    2d 23h
    $1,001–2,151

  10. Bus, train

    1. Take the bus from Portland Curbside Bus Stop to Vancouverbus bus
    2. Take the train from Vancouver to Toronto Union Stationtrain train
    3. Take the bus from Toronto to New Yorkbus bus
    4. Take the bus from New York to New Havenbus bus
    5. Take the train from New Haven to Old Saybrook Amtrak Stationtrain train
    4d 22h
    $838–1,963

Portland to Chester by train and bus

Calendar7Weekly Services
Duration2d 21hAverage Duration
Ticket$959Cheapest Price
See schedules

Questions & Answers

Map of how to get from Portland to Chester.ExpandLaunch map view
  • Distance: 2,519.2 mi
  • Duration: 10h 57m

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

You can take a bus from Portland Curbside Bus Stop to Chester Park & Ride @ W Main St via Pasco Bus Stop, Denver Union Station, St Louis Bus Station, Port Authority Bus Terminal, New York, Hartford, and Asylum St @ Bushnell Park in around 3d 4h. Alternatively, you can take a train from Portland to Chester Center @ Water Street Parking Lot via Chicago Union Station, Ny Moynihan Train Hall At Penn Station, Old Saybrook Amtrak Station, and Stage Rd & Rt 1 in around 2d 23h.

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