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How to get fromChicago to Kingstonby plane, train, train (Amtrak), bus (Flixbus), car, or bus

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

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 Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    7h 59m
    $224–591

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

    cheapest
    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 125th Street - Harlemtrain train
    3. Take the train from 125th Street - Harlem to Poughkeepsietrain train
    4. Take the bus from Poughkeepsie Train Station to Broadway & Kingston City Hallbus bus
    10h 5m
    $126–550

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    20h 30m
    $282–581

  4. Bus

    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
    21h 35m
    $168–322

  5. Drive 819.4 mi

    1. Drive from Chicago to Kingstoncar car 819.4 mi
    13h 47m
    $150–216

  6. Fly Chicago Midway International Airport to Albany County Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany to Kingstonbus bus
    7h 27m
    $160–795

  7. Fly Chicago O'Hare International Airport to Albany County Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the bus from Albany to Kingstonbus bus
    7h 54m
    $130–645

Chicago to Kingston by train and bus (Amtrak)

Calendar7Weekly Services
Duration20h 30mAverage Duration
Ticket$282Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Kingston.ExpandLaunch map view
  • Distance: 828.9 mi
  • Duration: 7h 59m

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

Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $280–600 and the journey takes 18h 43m. Alternatively, you can take a bus from Chicago Bus Station to Broadway & Pine Grove @ YMCA via Newark, New York, Kingston, and Schwenk Dr & Frog Alley in around 21h 35m.

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