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Chicago to Chesapeake trains

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Trip Overview

The average train between Chicago and Chesapeake takes 24h 58m and the fastest train takes 23h 29m. The train runs, on average, 6 times per week from Chicago to Chesapeake. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

24h 58m
Duration
990 mi
Distance
$642
Average price
6 times a week
Frequency

Chicago to Chesapeake train times

Trains run 6 times a week between Chicago and Chesapeake. The service departs Chicago at 6:40 PM in the evening, which arrives into Chesapeake at 19:09:00. All services require a transfer, and take on average 24h 58m. The schedules shown below are for the next available departures.

Departing Tuesday, November 10, 2026

  •  → 

    Arrives next day

    AmtrakAmtrak23h 29m • 1 change

Departing Wednesday, November 11, 2026

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    Arrives next day

    AmtrakAmtrak23h 29m • 1 change

Departing Thursday, November 12, 2026

  •  → 

    Arrives next day

    AmtrakAmtrak23h 29m • 1 change

Departing Friday, November 13, 2026

  •  → 

    Arrives next day

    AmtrakAmtrak27h 58m • 1 change

Departing Saturday, November 14, 2026

  •  → 

    Arrives next day

    AmtrakAmtrak27h 58m • 1 change

Departing Sunday, November 15, 2026

  •  → 

    Arrives next day

    AmtrakAmtrak23h 29m • 1 change

Frequently asked questions

Want to know about travelling from Chicago to Chesapeake? 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 Chesapeake.ExpandLaunch map view
  • Distance: 989.5 mi
  • Duration: 24h 58m

What companies run services between Chicago, IL, USA and Chesapeake, City of Chesapeake, VA, USA?

You can take a train from Chicago Union Station to Norfolk via Petersburg Amtrak Station in around 23h 41m.

Operators