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Duration 26h 6m
Distance 499 miles
Average price $141
Frequency 3/week

Trip overview

The train between Oakville and Chicago takes 26h 6m. The train runs, on average, 3 times per week from Oakville 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.


  1. Oakville
  2. Buffalo Depew Station
  3. Chicago
15h 45m
Bookable on Rome2rio
$106 - $180

Oakville to Chicago train times

Trains run three times a week between Oakville and Chicago. The service departs Oakville at 08:44 in the morning, which arrives into Chicago at 09:50. All services require a transfer at Buffalo (Depew) and take an average of 26h 6m. The schedules shown below are for the next available departures.

Frequently asked questions

Want to know about travelling from Oakville 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.

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No, there is no direct train from Oakville to Chicago station. However, there are services departing from Oakville and arriving at Chicago Union Station via Buffalo Depew Station. The journey, including transfers, takes approximately 15h 45m.

More details

The distance between Oakville and Chicago is 420 miles. The road distance is 499 miles.

Get driving directions

Oakville to Chicago train services, operated by VIA Rail, depart from Oakville station.

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Oakville to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.

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Book your Oakville to Chicago train tickets online with Omio and Omio.

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Chicago is 1h behind Oakville. It is currently 12:04 PM in Oakville and 11:04 AM in Chicago.

There are 2576+ hotels available in Chicago. Prices start at $100 USD per night.

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