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

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

    best
    1. Take the train from Greenport to Ronkonkomatrain train
    2. Take the train from Ronkonkoma to Woodsidetrain train
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    8h 3m
    $158–617

  2. Car ferry, train, train to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the carferry from Orient Point to New Londoncarferry car ferry
    2. Take the train from New London to New Haventrain train
    3. Take the train from New Haven to Windsor Lockstrain train
    4. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    10h 25m
    $104–479

  3. Train

    1. Take the train from Greenport to Ronkonkomatrain train
    2. Take the train from Ronkonkoma to New York Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train
    23h 33m
    $253–654

  4. Bus

    1. Take the bus from Greenport to 79th St & Broadwaybus bus Westbound-Westside Dropoff
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    24h 27m
    $176–295

  5. Drive  886.9 mi

    1. Drive from Greenport to Chicagocar car 886.9 mi
    15h 11m
    $162–234

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

    1. Take the train from Greenport to Ronkonkomatrain train
    2. Take the train from Ronkonkoma to New York Penn Stationtrain train
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    8h 6m
    $166–937

  7. Train, train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Greenport to Ronkonkomatrain train
    2. Take the train from Ronkonkoma to Woodsidetrain train
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 54m
    $228–717

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

    1. Take the train from Greenport to Ronkonkomatrain train
    2. Take the train from Ronkonkoma to Jamaicatrain train
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    10h 5m
    $132–627

  9. Car ferry, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the carferry from Orient Point to New Londoncarferry car ferry
    2. Take the train from New London to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    9h 39m
    $120–564

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

    1. Take the carferry from Orient Point to New Londoncarferry car ferry
    2. Take the train from New London to New Haventrain train
    3. Take the train from New Haven to Windsor Lockstrain train
    4. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    10h 7m
    $124–569

  11. Car ferry, train to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Take the carferry from Orient Point to New Londoncarferry car ferry
    2. Take the train from New London to New Haventrain train
    3. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    9h 13m
    $153–521

  12. Bus via Baltimore

    1. Take the bus from Greenport to Boerum Hill-Atlantic & 4 Avbus bus
    2. Take the bus from New York to Baltimorebus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    28h 40m
    $191–350

Greenport to Chicago by train

Calendar10Weekly Trains
Duration23h 33mAverage Duration
Ticket$253Cheapest Price
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Comparing Your Travel Options

Map of how to get from Greenport to Chicago.ExpandLaunch map view
  • Distance: 848.7 mi
  • Duration: 8h 3m

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

You can take a train from Greenport to Chicago Union Station via Ronkonkoma, Penn Station, and Ny Moynihan Train Hall At Penn Station in around 23h 33m. Alternatively, you can take a bus from Greenport to Chicago Bus Station via 79th St & Broadway, 79 St, 34 St-Penn Station, and New York Midtown in around 24h 27m.

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