Rome2Rio

How to get fromChicago to Milwaukieby plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

Find Transport to Milwaukie

See all options

There are 6 ways to get from Chicago to Milwaukie by plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly from Chicago O'Hare International Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX)plane plane ORD - PDX
    7h 45m
    $178–311

  2. Fly from Chicago Midway International Airport

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)plane plane MDW - PDX
    7h 35m
    $168–761

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Portlandtrain train Empire Builder
    46h 55m
    $1,238–1,898

  4. Bus

    1. Take the bus from Chicago Bus Station to Denver Union Stationbus bus
    2. Take the bus from Denver Union Station to Pasco Bus Stopbus bus
    3. Take the bus from Pasco Bus Stop to Portland Curbside Bus Stopbus bus
    2d 4h
    $430–648

  5. Drive  2,080.1 mi

    1. Drive from Chicago to Milwaukiecar car 2,080.1 mi
    33h 50m
    $380–549

  6. Train to General Mitchell International Airport, fly

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Portland International Airport (PDX)plane plane MKE - PDX
    10h 31m
    $225–572

Chicago to Milwaukie by train and tram (Amtrak)

Calendar7Weekly Services
Duration46h 55mAverage Duration
Ticket$1,238Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Chicago to Milwaukie.ExpandLaunch map view
  • Distance: 1,771.3 mi
  • Duration: 7h 45m

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

Alaska Airlines, Inc., American Airlines, and two other airlines fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX) every 3 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Portland once daily. Tickets cost $1,200–1,900 and the journey takes 46h 12m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Booking & Getting There