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How to get fromPort Jefferson to Chicagoby train, plane, train (Amtrak), bus (Flixbus), car, car ferry, or bus

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There are 10 ways to get from Port Jefferson to Chicago by train, plane, train (Amtrak), bus (Flixbus), car, car ferry, 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. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the train from Stony Brook to Jamaicatrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    7h 4m
    $335–893

  2. Car ferry, train to Bradley International Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the carferry from Port Jefferson to Bridgeportcarferry car ferry
    2. Take the train from New Haven to Windsor Lockstrain train
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 35m
    $120–556

  3. Train

    1. Take the train from Ronkonkoma to New York Penn Stationtrain train Ronkonkoma Branch
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    23h 6m
    $245–632

  4. Bus

    1. Take the bus from Manorville to 86 St & Central Park Westbus bus Sag Harbor-Westbound / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    26h 19m
    $193–375

  5. Drive  846.3 mi

    1. Drive from Port Jefferson to Chicagocar car 846.3 mi
    14h 22m
    $155–224

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

    1. Take the train from Huntington to New York Penn Stationtrain train
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    8h 4m
    $158–918

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

    1. Take the train from Stony Brook to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    8h 7m
    $152–595

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

    1. Take the train from Stony Brook to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 57m
    $222–695

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

    1. Take the carferry from Port Jefferson to Bridgeportcarferry car ferry
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h 13m
    $128–656

  10. Train, bus

    1. Take the train from Ronkonkoma to New York Penn Stationtrain train
    2. Take the bus from New York to Baltimorebus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    27h 1m
    $170–307

Port Jefferson to Chicago by bus and train

Calendar10Weekly Services
Duration23h 6mAverage Duration
Ticket$245Cheapest Price
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Comparing Your Travel Options

Map of how to get from Port Jefferson to Chicago.ExpandLaunch map view
  • Distance: 808.7 mi
  • Duration: 7h 4m

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

You can take a bus from NYS 25A/E Broadway to Chicago Union Station via Ronkonkoma LIRR, Ronkonkoma, Penn Station, and Ny Moynihan Train Hall At Penn Station in around 23h 6m. Alternatively, you can take a bus from NYS 25A/E Broadway to Chicago Bus Station via Ronkonkoma LIRR, Islip Airport Connection, Manorville, 86 St & Central Park West, 86 St, 34 St-Herald Sq, and New York Midtown in around 26h 19m.

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