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How to get fromManhattan to Chicagoby plane, bus (Flixbus), train (Amtrak), car, bus, train, or bus (Greyhound)

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There are 10 ways to get from Manhattan to Chicago by plane, bus (Flixbus), train (Amtrak), car, bus, 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 30m
    $205–662

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

    cheapest
    1. Take the train from 125th Street - Harlem to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 50m
    $123–621

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    20h 25m
    $150–240

  4. Train

    1. Take the train from 125th Street - Harlem to Croton-Harmontrain train Hudson
    2. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 48m
    $510–816

  5. Drive  792.4 mi

    1. Drive from Manhattan to Chicagocar car 792.4 mi
    13h 13m
    $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 51m
    $135–562

  7. Bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Port Authority Bus Terminal to Terminal Bbus bus
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 11m
    $137–820

  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 7m
    $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 48m
    $175–975

  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 20m
    $172–263

Manhattan to Chicago by bus (Flixbus)

Calendar14Weekly Buses
Duration20h 25mAverage Duration
Ticket$150Cheapest Price
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Comparing Your Travel Options

Map of how to get from Manhattan to Chicago.ExpandLaunch map view
  • Distance: 741.1 mi
  • Duration: 4h 30m

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

Southwest Airlines flies from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $150–240 and the journey takes 20h 25m.

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