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Chicago to Windsor & Cassopolis buses

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Trip Overview

The bus between Chicago and Windsor & Cassopolis takes 6h 50m. The bus runs, on average, once a week from Chicago to Windsor & Cassopolis. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

6h 50m
Duration
112 mi
Distance
$31
Average price
Once a week
Frequency

Chicago to Windsor & Cassopolis bus times

Buses run once a week between Chicago and Windsor & Cassopolis. The service departs Chicago at 9:30 PM at night, which arrives into Windsor & Cassopolis at 05:20:00. All services require a transfer at Elkhart Amtrak Station and take an average of 6h 50m. The schedules shown below are for the next available departures.

Departing Sunday, October 11, 2026

  •  → 

    Arrives next day

    AmtrakInterurban Trolley6h 50m • 1 change

Frequently asked questions

Want to know about travelling from Chicago to Windsor & Cassopolis? 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 Windsor & Cassopolis.ExpandLaunch map view
  • Distance: 111.7 mi
  • Duration: 6h 50m

What companies run services between Chicago, IL, USA and Windsor & Cassopolis, IN, USA?

Amtrak operates a bus from Chicago Union Station to Elkhart Amtrak Station once a week. Tickets cost $24–35 and the journey takes 1h 49m.

Operators