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Chicago to Oakville trains

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Trip Overview

The average train between Chicago and Oakville takes 20h 56m and the fastest train takes 20h 46m. The train runs, on average, 6 times per week from Chicago to Oakville. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

20h 56m
Duration
786 km
Distance
$397
Average price
6 times a week
Frequency

Chicago to Oakville train times

Trains run 6 times a week between Chicago and Oakville. The service departs Chicago at 9:30 PM at night, which arrives into Oakville at 19:16:00. All services require a transfer at Detroit and take an average of 20h 56m. The schedules shown below are for the next available departures.

Departing Friday, October 30, 2026

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    Arrives next day

    AmtrakVIA Rail20h 46m • 1 change

Departing Saturday, October 31, 2026

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    Arrives next day

    AmtrakVIA Rail21h 46m • 1 change

Departing Sunday, November 1, 2026

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    Arrives next day

    AmtrakVIA Rail20h 46m • 1 change

Departing Monday, November 2, 2026

  •  → 

    Arrives next day

    AmtrakVIA Rail20h 46m • 1 change

Departing Tuesday, November 3, 2026

  •  → 

    Arrives next day

    AmtrakVIA Rail20h 46m • 1 change

Departing Wednesday, November 4, 2026

  •  → 

    Arrives next day

    AmtrakVIA Rail20h 46m • 1 change

Frequently asked questions

Want to know about travelling from Chicago to Oakville? 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 Chicago to Oakville.ExpandLaunch map view
  • Distance: 785.7 km
  • Duration: 20h 56m

What companies run services between Chicago, IL, USA and Oakville, ON, Canada?

You can take a train from Chicago Union Station to Oakville via Detroit and Windsor in around 10h 18m.

Operators