Rome2Rio

Chicago to Chester buses

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Trip Overview

The average bus between Chicago and Chester takes 35h 23m and the fastest bus takes 27h 5m. The bus runs, on average, 5 times per week from Chicago to Chester. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

35h 23m
Duration
1,136 mi
Distance
$212
Average price
5 times a week
Frequency

Chicago to Chester bus times

Buses run 5 times a week between Chicago and Chester. The earliest departure is at 12:25 PM in the afternoon, and the last departure from Chicago is at 7:15 PM which arrives into Chester at 1:00 PM. All services require a transfer at New York Midtown and take an average of 35h 23m. The schedules shown below are for the next available departures.

Departing Wednesday, November 11, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USACT Transit40h 45m • 2 changes

Departing Thursday, November 12, 2026

  •  → 

    Arrives next day

    Flixbus USAFlixbus USACT Transit27h 5m • 2 changes

Departing Saturday, November 14, 2026

  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USACT Transit41h 18m • 2 changes
  •  → 

    Arrives +2 days

    Flixbus USAFlixbus USACT Transit40h 45m • 2 changes

Departing Sunday, November 15, 2026

  •  → 

    Arrives next day

    Flixbus USAFlixbus USACT Transit27h 5m • 2 changes

Frequently asked questions

Want to know about travelling from Chicago to Chester? 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 Chester.ExpandLaunch map view
  • Distance: 1,136.4 mi
  • Duration: 35h 23m

What companies run services between Chicago, IL, USA and Chester, CT, USA?

You can take a bus from Chicago Bus Station to Chester Park & Ride @ W Main St via New York Midtown, Hartford, Union Station, and Asylum St @ Bushnell Park in around 25h 20m.

Operators