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Pittsfield to Chicago buses

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Trip Overview

The bus between Pittsfield and Chicago takes 21h 40m. The bus runs, on average, 4 times per week from Pittsfield 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.

21h 40m
Duration
1,140 mi
Distance
$240
Average price
4 times a week
Frequency

Pittsfield to Chicago bus times

Buses run 4 times a week between Pittsfield and Chicago. The service departs Pittsfield at 4:45 PM in the afternoon, which arrives into Chicago at 13:25:00. All services require a transfer at New York and take an average of 21h 40m. The schedules shown below are for the next available departures.

Departing Saturday, November 14, 2026

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    Arrives next day

    Peter Pan Bus LinesNJ TransitFlixbus USA21h 40m • 2 changes

Departing Sunday, November 15, 2026

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    Arrives next day

    Peter Pan Bus LinesNJ TransitFlixbus USA21h 40m • 2 changes

Departing Monday, November 16, 2026

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    Arrives next day

    Peter Pan Bus LinesNJ TransitFlixbus USA21h 40m • 2 changes

Departing Thursday, November 19, 2026

  •  → 

    Arrives next day

    Peter Pan Bus LinesNJ TransitFlixbus USA21h 40m • 2 changes

Frequently asked questions

Want to know about travelling from Pittsfield 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 Pittsfield to Chicago.ExpandLaunch map view
  • Distance: 1,139.9 mi
  • Duration: 21h 40m

What companies run services between Pittsfield, MA, USA and Chicago, IL, USA?

You can take a bus from Pittsfield to Chicago Bus Station via New York, Port Authority Bus Terminal, and Newark Penn Station in around 25h 32m.

Operators