Rome2Rio

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

Find Transport to Chicago

See all options

There are 9 ways to get from Oyster Bay to Chicago by taxi, plane, bus (Flixbus), train (Amtrak), 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 21m
    $263–657

  2. Drive 818.2 mi

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

  3. Bus

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    19h 16m
    $200–292

  4. Train (Amtrak)

    1. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 53m
    $320–672

  5. 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
    $193–574

  6. 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 38m
    $329–880

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

    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 53m
    $223–674

  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 26m
    $192–905

  9. Bus via Baltimore

    1. Take the bus from Port Authority Bus Terminal to Baltimorebus bus New York
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    25h 24m
    $206–324

Oyster Bay to Chicago by train and bus

Calendar22Weekly Services
Duration19h 16mAverage Duration
Ticket$200Cheapest Price
See schedules

Questions & Answers

Map of how to get from Oyster Bay to Chicago.ExpandLaunch map view
  • Distance: 797.5 mi
  • Duration: 4h 21m

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

Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–240 and the journey takes 16h 55m. Jefferson Lines also services this route once daily. Alternatively, Amtrak operates a train from Ny Moynihan Train Hall At Penn Station to Chicago Union Station once daily. Tickets cost $310–650 and the journey takes 19h 32m.

Airlines
Train operators
Bus operators
Other 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