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How to get fromGrand Central Terminal to Chicagoby plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound)

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There are 10 ways to get from Grand Central Terminal to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound)

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 Laguardia Airport to Chicago Midway International Airport

    best
    1. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    4h 40m
    $211–672

  2. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Grand Central Terminal to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 49m
    $114–572

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    19h 57m
    $250–550

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    20h 50m
    $150–230

  5. Drive  790.9 mi

    1. Drive from Grand Central Terminal to Chicagocar car 790.9 mi
    13h 10m
    $145–209

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

    1. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    4h 53m
    $141–572

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

    1. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 1m
    $326–873

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

    1. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 16m
    $143–882

  9. Train to Philadelphia International Airport, fly to Chicago Midway International Airport

    1. Take the train from Ny Moynihan Train Hall At Penn Station to 30th Street Stationtrain train
    2. Fly from Philadelphia International Airport (PHL) to Chicago Midway International Airport (MDW)plane plane PHL - MDW
    6h 8m
    $166–974

  10. Bus via Baltimore (Greyhound)

    1. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus Greyhound US0670 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    23h 36m
    $147–248

Grand Central Terminal to Chicago by foot and bus (Greyhound)

Calendar14Weekly Services
Duration23h 36mAverage Duration
Ticket$147Cheapest Price
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Comparing Your Travel Options

Map of how to get from Grand Central Terminal to Chicago.ExpandLaunch map view
  • Distance: 745.3 mi
  • Duration: 4h 40m

What companies run services between Grand Central Terminal, NY, USA and Chicago, IL, USA?

Southwest Airlines and Delta fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) every 2 hours. Alternatively, Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $250–550 and the journey takes 19h 32m.

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