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How to get fromChicago to Port Chesterby subway, plane, train, train (Amtrak), bus (Flixbus), car, shuttle, or bus

Find Transport to Port Chester

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There are 9 ways to get from Chicago to Port Chester by subway, plane, train, train (Amtrak), bus (Flixbus), car, shuttle, 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. Subway to Chicago Midway International Airport, fly to Laguardia Airport, train

    best
    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    3. Take the train from 125th Street - Harlem to Port Chestertrain train
    5h 17m
    $214–678

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, line 13 bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from Main St @ S Broadway to Westchester Ave @ Smith Stbus bus
    6h 16m
    $88–461

  3. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain train Hudson
    21h 32m
    $528–813

  4. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    23h 4m
    $164–241

  5. Drive  810.4 mi

    1. Drive from Chicago to Port Chestercar car 810.4 mi
    13h 36m
    $148–214

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Port Chestertrain train
    5h 37m
    $144–578

  7. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Port Chestertrain train
    5h 49m
    $336–889

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take a shuttle bus from Newark Airport Terminal B to Grand Centralshuttle bus
    3. Take the train from Grand Central Terminal to Port Chestertrain train
    6h 20m
    $166–821

  9. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to Port Chestertrain train
    23h 41m
    $193–309

Chicago to Port Chester by train

Calendar7Weekly Trains
Duration21h 32mAverage Duration
Ticket$528Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Port Chester.ExpandLaunch map view
  • Distance: 762.2 mi
  • Duration: 5h 17m

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

You can take a train from Chicago Union Station to Port Chester via Croton-Harmon and 125th Street - Harlem in around 21h 32m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown twice daily. Tickets cost $150–240 and the journey takes 20h 10m.

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