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Chicago to Upland trains

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Trip Overview

The average train between Chicago and Upland takes 42h 46m and the fastest train takes 42h 24m. The train runs, on average, 5 times per week from Chicago to Upland. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

42h 46m
Duration
2,176 mi
Distance
$1,407
Average price
5 times a week
Frequency

Chicago to Upland train times

Trains run 5 times a week between Chicago and Upland. The service departs Chicago at 2:25 PM in the afternoon, which arrives into Upland at 07:12:00. All services require a transfer at San Bernardino and take an average of 42h 46m. The schedules shown below are for the next available departures.

Departing Friday, October 30, 2026

  •  → 

    Arrives +2 days

    AmtrakMetrolink Trains43h 47m • 1 change

Departing Saturday, October 31, 2026

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    Arrives +2 days

    AmtrakMetrolink Trains42h 54m • 1 change

Departing Sunday, November 1, 2026

  •  → 

    Arrives +2 days

    AmtrakMetrolink Trains42h 24m • 1 change

Departing Monday, November 2, 2026

  •  → 

    Arrives +2 days

    AmtrakMetrolink Trains42h 24m • 1 change

Departing Tuesday, November 3, 2026

  •  → 

    Arrives +2 days

    AmtrakMetrolink Trains42h 24m • 1 change

Frequently asked questions

Want to know about travelling from Chicago to Upland? 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 Upland.ExpandLaunch map view
  • Distance: 2,176.4 mi
  • Duration: 42h 46m

What companies run services between Chicago, IL, USA and Upland, CA, USA?

Amtrak operates a train from Chicago Union Station to San Bernardino once daily. Tickets cost $1,100–1,900 and the journey takes 41h 21m.

Operators