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Oyster Bay to Chicago trains

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Trip Overview

The average train between Oyster Bay and Chicago takes 27h 10m and the fastest train takes 22h 35m. The train runs, on average, 3 times per week from Oyster Bay to Chicago. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

27h 10m
Duration
991 mi
Distance
$616
Average price
3 times a week
Frequency

Oyster Bay to Chicago train times

Trains run 3 times a week between Oyster Bay and Chicago. The earliest departure is at 12:37 PM in the afternoon, and the last departure from Oyster Bay is at 10:52 PM which arrives into Chicago at 10:12 AM. All services require a transfer at Jamaica and take an average of 27h 10m. The schedules shown below are for the next available departures.

Departing Saturday, October 24, 2026

  •  → 

    Arrives next day

    Long Island Rail RoadLong Island Rail RoadAmtrak22h 35m • 2 changes

Departing Sunday, October 25, 2026

  •  → 

    Arrives next day

    Long Island Rail RoadLong Island Rail RoadAmtrak22h 35m • 2 changes
  •  → 

    Arrives +2 days

    Long Island Rail RoadLong Island Rail RoadAmtrak36h 20m • 2 changes

Frequently asked questions

Want to know about travelling from Oyster Bay to Chicago? We have put together a list of the most frequently asked questions from our users such as: What is the cheapest mode of transport? What is the quickest option? How much do tickets usually cost? and many more.

Map of how to get from Oyster Bay to Chicago.ExpandLaunch map view
  • Distance: 991.1 mi
  • Duration: 27h 10m

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 $500–850 and the journey takes 19h 32m.

Operators