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Chicago to Westbrook trains

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Trip Overview

The average train between Chicago and Westbrook takes 25h 34m and the fastest train takes 22h 55m. The train runs, on average, 6 times per week from Chicago to Westbrook. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

25h 34m
Duration
1,006 mi
Distance
$640
Average price
6 times a week
Frequency

Chicago to Westbrook train times

Trains run 6 times a week between Chicago and Westbrook. The service departs Chicago at 9:30 PM at night, which arrives into Westbrook at 21:25:00. All services require a transfer at Springfield and take an average of 25h 34m. The schedules shown below are for the next available departures.

Departing Wednesday, October 28, 2026

  •  → 

    Arrives next day

    AmtrakAmtrakAmtrak22h 55m • 2 changes

Departing Thursday, October 29, 2026

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    Arrives next day

    AmtrakAmtrakAmtrak22h 55m • 2 changes

Departing Friday, October 30, 2026

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    Arrives +2 days

    AmtrakAmtrakAmtrak36h 19m • 2 changes

Departing Saturday, October 31, 2026

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    Arrives next day

    AmtrakAmtrakAmtrak25h 30m • 2 changes

Departing Sunday, November 1, 2026

  •  → 

    Arrives next day

    AmtrakAmtrakAmtrak22h 55m • 2 changes

Departing Monday, November 2, 2026

  •  → 

    Arrives next day

    AmtrakAmtrakAmtrak22h 55m • 2 changes

Frequently asked questions

Want to know about travelling from Chicago to Westbrook? 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 Westbrook.ExpandLaunch map view
  • Distance: 1,006.1 mi
  • Duration: 25h 34m

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

You can take a train from Chicago Union Station to Westbrook via Springfield and New Haven in around 22h 49m.

Operators