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How to get fromChicago to Pine Plainsby plane, car, train (Amtrak), bus, taxi, or train

Find Transport to Pine Plains

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There are 10 ways to get from Chicago to Pine Plains by plane, car, train (Amtrak), bus, taxi, 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 Chicago Midway International Airport to Bradley International Airport, drive

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Drive from Hartford-Airport-BDL to Pine Plainscar car
    5h 18m
    $162–871

  2. Fly Chicago O'Hare International Airport to Bradley International Airport, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Drive from Hartford-Airport-BDL to Pine Plainscar car
    5h 38m
    $108–521

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Rhinecliff Amtrak Stationtrain train Lake Shore Limited
    18h 52m
    $579–865

  4. Bus, taxi

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark to New Yorkbus bus
    3. Take the bus from New York to Kingstonbus bus
    4. Take the taxi from Kingston to Pine Plainstaxi taxi
    24h 19m
    $327–510

  5. Drive  839.8 mi

    1. Drive from Chicago to Pine Plainscar car 839.8 mi
    14h 10m
    $149–215

  6. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Rhinecliff Amtrak Stationtrain train
    7h 23m
    $360–866

  7. Fly Chicago Midway International Airport to Albany County Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Rhinecliff Amtrak Stationtrain train
    7h 6m
    $278–1,188

  8. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Rhinecliff Amtrak Stationtrain train
    7h 37m
    $280–889

  9. Fly Chicago O'Hare International Airport to Albany County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Rhinecliff Amtrak Stationtrain train
    7h 39m
    $218–838

  10. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Wassaictrain train
    8h 38m
    $176–484

Chicago Midway International Airport (MDW) to Bradley International Airport (BDL) flights

Calendar24Weekly Planes
Duration2h 49mAverage Duration
Ticket$157Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Chicago to Pine Plains.ExpandLaunch map view
  • Distance: 845.7 mi
  • Duration: 5h 18m

What companies run services between Chicago, IL, USA and Pine Plains, NY, USA?

Amtrak operates a train from Chicago Union Station to Rhinecliff Amtrak Station once daily. Tickets cost $470–750 and the journey takes 18h 25m.

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