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

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There are 12 ways to get from Madison to Chicago by train, plane, bus (Flixbus), train (Amtrak), car, bus, 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 Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the train from Madison to Newark Broad Sttrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 44m
    $166–873

  2. Bus

    cheapest
    1. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2641 / ...
    18h 46m
    $135–236

  3. Train via Ossining

    1. Take the train from Madison to New York Penn Stationtrain train Mne
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Croton-Harmon Amtrak Stationtrain train
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    22h 26m
    $313–687

  4. Drive 764.2 mi

    1. Drive from Madison to Chicagocar car 764.2 mi
    12h 46m
    $140–202

  5. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Madison to New York Penn Stationtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 45m
    $188–573

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

    1. Take the train from Madison to New York Penn Stationtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 6m
    $218–673

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

    1. Take the train from Madison to New York Penn Stationtrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 8m
    $329–889

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

    1. Take the train from Newark 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 36m
    $168–1,029

  9. Fly Newark Liberty International Airport to General Mitchell International Airport, train

    1. Fly from Newark Liberty International Airport (EWR) to General Mitchell International Airport (MKE)plane plane EWR - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 59m
    $583–892

  10. Train, bus to Lehigh Valley International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Madison to New York Penn Stationtrain train
    2. Take the bus from New York to Allentown Airportbus bus
    3. Fly from Lehigh Valley International Airport (ABE) to Chicago O'Hare International Airport (ORD)plane plane ABE - ORD
    8h 24m

  11. Bus via Baltimore

    1. Take the bus from Newark Penn Station to Baltimorebus bus New York / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    25h 55m
    $154–356

  12. Train (Amtrak)

    1. Take the train from Newark Penn Station to Chicago Union Stationtrain train Cardinal
    30h 13m
    $364–766

Madison to Chicago by train and bus

Calendar22Weekly Services
Duration18h 46mAverage Duration
Ticket$135Cheapest Price
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Questions & Answers

Map of how to get from Madison to Chicago.ExpandLaunch map view
  • Distance: 759.9 mi
  • Duration: 5h 44m

What companies run services between Madison, NJ, USA and Chicago, IL, USA?

Flixbus USA operates a bus from Newark Penn Station to Chicago Bus Station twice daily. Tickets cost $130–220 and the journey takes 16h 20m. FlixBus-us also services this route once daily. Alternatively, you can take a train from Madison to Chicago Union Station via Penn Station, Ny Moynihan Train Hall At Penn Station, and Croton-Harmon Amtrak Station in around 22h 26m.

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