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

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There are 11 ways to get from Port Chester to Chicago by train, bus, 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, bus to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Port Chester to 125th Street - Harlemtrain train
    2. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 32m
    $98–516

  2. Train, bus to Laguardia Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Port Chester to 125th Street - Harlemtrain train
    2. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 50m
    $63–276

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    21h 23m
    $120–385

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    24h 25m
    $98–233

  5. Drive 810.3 mi

    1. Drive from Port Chester to Chicagocar car 810.3 mi
    13h 33m
    $148–214

  6. Train, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Port Chester to Grand Central Terminaltrain train
    2. Take the bus from Grand Central to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 31m

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Port Chester to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 10m
    $775–1,038

  8. Fly Westchester County Airport to Chicago O'Hare International Airport

    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 25m
    $63–311

  9. Train, bus to Newark Liberty International Airport, fly to Chicago Midway International Airport

    1. Take the train from Port Chester to Grand Central Terminaltrain train
    2. Take the bus from Grand Central to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago Midway International Airport (MDW)plane plane EWR - MDW
    6h 23m

  10. Fly Laguardia Airport to General Mitchell International Airport, train

    1. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 2m
    $225–631

  11. Train, bus

    1. Take the train from Port Chester to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    24h 38m
    $117–227

Port Chester to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration21h 23mAverage Duration
Ticket$120Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Croton-Harmon Amtrak Station to Chicago Union Station once daily. Tickets cost $110–370 and the journey takes 18h 46m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $90–150 and the journey takes 20h 25m.

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