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Chicago to Milwaukie trains

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Trip Overview

The train between Chicago and Milwaukie takes 46h 55m. The train runs, on average, 2 times per week from Chicago to Milwaukie. The journey time may be longer on weekends and holidays; use the search form on this page to search for a specific travel date.

46h 55m
Duration
2,249 mi
Distance
$1,464
Average price
Twice a week
Frequency

Chicago to Milwaukie train times

Trains run twice a week between Chicago and Milwaukie. The service departs Chicago at 3:05 PM in the afternoon, which arrives into Milwaukie at 12:00:55. All services require a transfer at Portland and take an average of 46h 55m. The schedules shown below are for the next available departures.

Departing Thursday, October 22, 2026

  •  → 

    Arrives +2 days

    AmtrakPortland TriMet46h 55m • 1 change

Departing Friday, October 23, 2026

  •  → 

    Arrives +2 days

    AmtrakPortland TriMet46h 55m • 1 change

Frequently asked questions

Want to know about travelling from Chicago to Milwaukie? 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 Milwaukie.ExpandLaunch map view
  • Distance: 2,249.1 mi
  • Duration: 46h 55m

What companies run services between Chicago, IL, USA and Milwaukie, OR, USA?

Amtrak operates a train from Chicago Union Station to Portland once daily. Tickets cost $1,200–2,000 and the journey takes 46h 12m.

Operators