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

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There are 10 ways to get from Chicago to Port Chester by subway, plane, train, train (Amtrak), bus, car, 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 Roosevelt 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 12m
    $94–497

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

    cheapest
    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 34m
    $64–307

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    21h 16m
    $254–547

  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 57m
    $189–374

  5. Drive 810.4 mi

    1. Drive from Chicago to Port Chestercar car 810.4 mi
    13h 34m
    $148–214

  6. 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 50m
    $70–299

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Grand Central Terminal to Port Chestertrain train
    6h 2m
    $86–312

  8. Fly Chicago O'Hare International Airport to Westchester County Airport, line 0013 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 15m
    $448–611

  9. Fly Chicago Midway International Airport to Philadelphia International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Grand Central Terminal to Port Chestertrain train
    7h 7m
    $120–1,177

  10. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    23h 7m
    $128–216

Chicago to Port Chester by train and bus (Amtrak)

Calendar7Weekly Services
Duration21h 16mAverage Duration
Ticket$254Cheapest Price
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Questions & Answers

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 $240–550 and the journey takes 19h 23m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown once daily. Tickets cost $120–210 and the journey takes 20h 10m.

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