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

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There are 12 ways to get from Madison to Chicago by plane, bus (Flixbus), train (Amtrak), car, train, or bus

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 Newark Liberty International Airport to Chicago O'Hare International Airport

    best
    1. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    5h 53m
    $117–676

  2. Bus (Flixbus)

    1. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2640 / ...
    22h 6m
    $156–239

  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
    $520–845

  4. Drive  764.2 mi

    1. Drive from Madison to Chicagocar car 764.2 mi
    12h 46m
    $131–189

  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 55m
    $218–675

  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 12m
    $128–495

  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 17m
    $369–891

  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 47m
    $178–934

  9. Bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Madison, NJ to NYC - 43th St & Madison Avebus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 53m
    $159–720

  10. 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
    8h 1m
    $152–710

  11. Train, bus

    1. Take the train from Madison to New York Penn Stationtrain train Mne
    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
    25h 16m
    $173–292

  12. Train (Amtrak)

    1. Take the train from Newark Penn Station to Chicago Union Stationtrain train Cardinal
    30h 13m
    $605–1,019

Madison to Chicago by train and bus (Flixbus)

Calendar28Weekly Services
Duration22h 6mAverage Duration
Ticket$156Cheapest Price
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Comparing Your Travel Options

Map of how to get from Madison to Chicago.ExpandLaunch map view
  • Distance: 759.9 mi
  • Duration: 5h 53m

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

American Airlines, United Airlines, and Delta fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Flixbus USA operates a bus from Newark Penn Station to Chicago Bus Station 4 times a day. Tickets cost $150–220 and the journey takes 19h 40m.

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