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

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There are 9 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 13m
    $114–521

  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 43m
    $88–411

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Rhinecliff Amtrak Stationtrain train Lake Shore Limited
    18h 52m
    $385–701

  4. Bus, taxi

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from New York to Kingstonbus bus
    4. Take the taxi from Kingston to Pine Plainstaxi taxi
    20h 16m
    $302–505

  5. Drive 839.8 mi

    1. Drive from Chicago to Pine Plainscar car 839.8 mi
    14h 7m
    $154–222

  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 24m
    $314–751

  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
    $258–1,038

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

    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
    3. Take the taxi from Rhinecliff Amtrak Station to Pine Plainstaxi taxi
    7h 33m
    $228–888

  9. 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
    $216–654

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

Calendar41Weekly Planes
Duration3h 13mAverage Duration
Ticket$101Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Pine Plains.ExpandLaunch map view
  • Distance: 845.7 mi
  • Duration: 5h 13m

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 $280–600 and the journey takes 18h 25m.

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