Rome2Rio

Orillia to Chicago buses

Find Transport to Chicago

View schedule

Trip Overview

The average bus between Orillia and Chicago takes 23h 9m and the fastest bus takes 17h 10m. The bus runs, on average, 5 times per week from Orillia 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.

23h 9m
Duration
598 mi
Distance
$108
Average price
5 times a week
Frequency

Orillia to Chicago bus times

Buses run 5 times a week between Orillia and Chicago. The earliest departure is at 7:05 PM in the evening, and the last departure from Orillia is at 7:05 PM which arrives into Chicago at 5:05 PM. All services require a transfer at Toronto Pearson Airport and take an average of 23h 9m. The schedules shown below are for the next available departures.

Departing Friday, October 9, 2026

  •  → 

    Arrives next day

    Flixbus USAFlixbus USAFlixbus USA17h 10m • 2 changes

Departing Saturday, October 10, 2026

  •  → 

    Arrives next day

    Flixbus USAFlixbus USAFlixbus USA17h 10m • 2 changes

Departing Sunday, October 11, 2026

  •  → 

    Arrives next day

    Flixbus USAFlixbus USAFlixbus USA17h 10m • 2 changes

Departing Monday, October 12, 2026

  •  → 

    Arrives next day

    Flixbus USAFlixbus USAFlixbus USA17h 15m • 2 changes

Departing Tuesday, October 13, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USAFlixbus USA47h • 2 changes

Frequently asked questions

Want to know about travelling from Orillia 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 Orillia to Chicago.ExpandLaunch map view
  • Distance: 598.2 mi
  • Duration: 23h 9m

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

You can take a bus from Orillia Downtown Terminal Bus Stop to Chicago Bus Station via Toronto Pearson Airport and Detroit Bus Station in around 16h.

Operators