Rome2Rio

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

Find Transport to Chicago

See all options

There are 10 ways to get from Port Jefferson to Chicago by train, plane, bus (Flixbus), train (Amtrak), 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 5m
    $335–893

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

    cheapest
    1. Take the car ferry 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 30m
    $115–514

  3. 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 N2641 / ...
    22h 49m
    $183–385

  4. 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 7m
    $325–682

  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
    $187–1,468

  7. 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 52m
    $172–595

  8. 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 13m
    $222–695

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

    1. Take the car ferry 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
    $120–547

  10. Train, bus

    1. Take the train from Ronkonkoma to New York Penn Stationtrain train
    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
    26h 18m
    $170–382

Port Jefferson to Chicago by bus and train

Calendar10Weekly Services
Duration23h 7mAverage Duration
Ticket$325Cheapest Price
See schedules

Questions & Answers

Map of how to get from Port Jefferson to Chicago.ExpandLaunch map view
  • Distance: 808.7 mi
  • Duration: 7h 5m

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 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 22h 49m. Alternatively, 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 7m.

Airlines
Train operators
Bus operators
Ferry operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

More Questions & Answers