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

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There are 9 ways to get from Chicago to Port Chester by subway, plane, train, train (Amtrak), bus, car, shuttle, or bus (Flixbus)

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
    $144–727

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

    cheapest
    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 55m
    $86–339

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    21h 13m
    $296–597

  4. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Port Chestertrain train
    22h 59m
    $170–354

  5. Drive 810.4 mi

    1. Drive from Chicago to Port Chestercar car 810.4 mi
    13h 33m
    $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 40m
    $94–367

  7. 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 29m
    $146–401

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

    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 18m
    $98–481

  9. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2642 / ...
    25h 33m
    $148–242

Chicago to Port Chester by train and bus (Amtrak)

Calendar7Weekly Services
Duration21h 13mAverage Duration
Ticket$296Cheapest Price
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Questions & Answers

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?

Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $280–600 and the journey takes 19h 23m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown 3 times a day. Tickets cost $140–240 and the journey takes 22h 40m.

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