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How to get fromKingston to Chicagoby train, plane, train (Amtrak), bus (Flixbus), or car

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There are 7 ways to get from Kingston to Chicago by train, plane, train (Amtrak), bus (Flixbus), or car

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

  1. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 5m
    $223–591

  2. Train to Albany County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain train
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    8h 32m
    $116–648

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    19h 42m
    $280–600

  4. Bus

    1. Take the bus from Kingston to New Yorkbus bus
    2. Take the bus from New York to Newarkbus bus
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    21h 37m
    $165–325

  5. Drive 818.4 mi

    1. Drive from Kingston to Chicagocar car 818.4 mi
    13h 45m
    $150–216

  6. Train to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain train
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    8h 4m
    $131–768

  7. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h 18m
    $121–520

Kingston to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration19h 42mAverage Duration
Ticket$280Cheapest Price
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Questions & Answers

Map of how to get from Kingston to Chicago.ExpandLaunch map view
  • Distance: 829.5 mi
  • Duration: 7h 5m

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

Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $280–600 and the journey takes 18h 2m. Alternatively, you can take a bus from Clinton & Greenkill to Chicago Bus Station via Schwenk Dr & Frog Alley, Kingston, New York, and Newark Penn Station in around 21h 37m.

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