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Toronto Union Station to Chicago Loop trains

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Trip Overview

The train between Toronto Union Station and Chicago Loop takes 26h 52m. The train runs, on average, 6 times per week from Toronto Union Station to Chicago Loop. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

26h 52m
Duration
509 mi
Distance
$287
Average price
6 times a week
Frequency

Toronto Union Station to Chicago Loop train times

Trains run 6 times a week between Toronto Union Station and Chicago Loop. The service departs Toronto Union Station at 8:20 AM in the morning, which arrives into Chicago Loop at 10:12:00. All services require a transfer at Windsor and take an average of 26h 52m. The schedules shown below are for the next available departures.

Departing Monday, November 9, 2026

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    Arrives next day

    VIA RailAmtrak26h 52m • 1 change

Departing Tuesday, November 10, 2026

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    Arrives next day

    VIA RailAmtrak26h 52m • 1 change

Departing Wednesday, November 11, 2026

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    Arrives next day

    VIA RailAmtrak26h 52m • 1 change

Departing Thursday, November 12, 2026

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    Arrives next day

    VIA RailAmtrak26h 52m • 1 change

Departing Friday, November 13, 2026

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    Arrives next day

    VIA RailAmtrak26h 52m • 1 change

Departing Saturday, November 14, 2026

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    Arrives next day

    VIA RailAmtrak26h 52m • 1 change

Frequently asked questions

Want to know about travelling from Toronto Union Station to Chicago Loop? 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 Toronto Union Station to Chicago Loop.ExpandLaunch map view
  • Distance: 509.5 mi
  • Duration: 26h 52m

What companies run services between Toronto Union Station, ON, Canada and Chicago Loop, IL, USA?

You can take a train from Toronto Union Station to Chicago Union Station via Windsor and Detroit in around 10h 38m.

Operators