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How to get fromPenn Station NY to Chicago Union Stationby train, plane, subway, bus (Flixbus), train (Amtrak), car, or bus (Greyhound)

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There are 10 ways to get from Penn Station NY to Chicago Union Station by train, plane, subway, bus (Flixbus), train (Amtrak), car, 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. Train to Laguardia Airport, fly to Chicago Midway International Airport, subway

    best
    1. Take the train from New York Penn Station to Flushing Main Streettrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    3. Take the subway from Midway to Quincysubway subway
    5h 7m
    $210–571

  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
    7h 30m
    $109–572

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    17h 11m
    $140–230

  4. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    19h 39m
    $300–650

  5. Drive 790.2 mi

    1. Drive from Penn Station NY to Chicago Union Stationcar car 790.2 mi
    13h 9m
    $145–209

  6. 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
    $142–882

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

    1. Take the train from New York Penn Station to Flushing Main Streettrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 31m
    $140–671

  8. 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 24m
    $326–873

  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
    5h 59m
    $176–974

  10. Bus via Baltimore

    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 16m
    $155–348

Penn Station NY to Chicago Union Station by foot and bus (Flixbus)

Calendar15Weekly Services
Duration17h 11mAverage Duration
Ticket$140Cheapest Price
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Questions & Answers

Map of how to get from Penn Station NY to Chicago Union Station.ExpandLaunch map view
  • Distance: 749.2 mi
  • Duration: 5h 7m

What companies run services between Penn Station NY, USA and Chicago Union Station, IL, USA?

Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–230 and the journey takes 16h 55m. Alternatively, Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $300–650 and the journey takes 19h 32m.

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