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How to get fromOyster Bay to Chicagoby taxi, plane, train (Amtrak), bus (Flixbus), car, train, or bus (Greyhound)

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There are 9 ways to get from Oyster Bay to Chicago by taxi, plane, train (Amtrak), bus (Flixbus), car, train, 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. Taxi to Westchester County Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the taxi from Oyster Bay to White-Plains-Airport-HPNtaxi taxi
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    4h 20m
    $273–757

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

    cheapest
    1. Take the train from Oyster Bay to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 45m
    $143–574

  3. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 52m
    $260–622

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    22h 45m
    $150–262

  5. Drive  818.2 mi

    1. Drive from Oyster Bay to Chicagocar car 818.2 mi
    13h 44m
    $150–216

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

    1. Take the train from Oyster Bay to Jamaicatrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 32m
    $213–674

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

    1. Take the train from Oyster Bay to Jamaicatrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    5h 39m
    $329–880

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

    1. Take the train from Oyster Bay to Jamaicatrain train
    2. Take the train from Jamaica to New York Penn Stationtrain train
    3. Take the train from New York Penn Station to Newark Airport Railroad Stationtrain train
    4. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 27m
    $153–905

  9. Bus via Baltimore (Greyhound)

    1. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus Greyhound US0670 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    25h 56m
    $156–284

Oyster Bay to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 52mAverage Duration
Ticket$260Cheapest Price
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Questions & Answers

Map of how to get from Oyster Bay to Chicago.ExpandLaunch map view
  • Distance: 797.5 mi
  • Duration: 4h 20m

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

Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $250–600 and the journey takes 19h 32m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–240 and the journey takes 20h 25m.

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