Rome2Rio

Chicago to Milwaukie trains

Find Transport to Milwaukie

View schedule
QR code to download the Rome2Rio app

Download the Rome2Rio travel app

Scan QR code with your phone to download the app

Download on the App StoreGet it on Google Play

Trip Overview

The average train between Chicago and Milwaukie takes 46h 56m and the fastest train takes 46h 55m. The train runs, on average, 5 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 56m
Duration
2,249 mi
Distance
$1,455
Average price
5 times a week
Frequency

Chicago to Milwaukie train times

Trains run 5 times a week between Chicago and Milwaukie. The service departs Chicago at 3:05 PM in the afternoon, which arrives into Milwaukie at 12:02:20. All services require a transfer at Portland and take an average of 46h 56m. The schedules shown below are for the next available departures.

Departing Wednesday, November 11, 2026

  •  → 

    Arrives +2 days

    AmtrakPortland TriMet46h 57m • 1 change

Departing Thursday, November 12, 2026

  •  → 

    Arrives +2 days

    AmtrakPortland TriMet46h 55m • 1 change

Departing Friday, November 13, 2026

  •  → 

    Arrives +2 days

    AmtrakPortland TriMet46h 55m • 1 change

Departing Saturday, November 14, 2026

  •  → 

    Arrives +2 days

    AmtrakPortland TriMet46h 57m • 1 change

Departing Sunday, November 15, 2026

  •  → 

    Arrives +2 days

    AmtrakPortland TriMet46h 57m • 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 56m

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 $1,200–1,900 and the journey takes 46h 12m.

Operators