As Easy As...
There are lots of hard ways but only one easy way to get from Chicago to Portland - take the train.
Chicago must be the rail capital of America. Not only do they have a dozen or so intercontinental trains leaving daily, they have five major train stations. This was once the main boarding area at Union Station (now everyone descends one or more levels) and the station handles all the Amtrak passenger trains and some commuter traffic (50,000 passengers a day. Also downtown is Ogilvie Transportation Center (40,000 commuters a day), Millennium Station (20,000 passengers daily), La Salle St. Station (16,000 daily) and Van Buren Street Station (10,000 per day). Most of these stations have been operating in one form or another since the 1850s.
Here passengers are heading for our train, the Empire Builder. From Chicago the train passes through Wisconsin, Minnesota, North Dakota, Montana, Idaho then splits in eastern Washington. Most of the cars continue on to Seattle. A smaller train is formed to go to Portland, Oregon, our destination.
We briefly play peek-a-boo with downtown Chicago before heading north to Milwaukee, our first major stop. For a January, it sure doesn't look like winter.
Though there are rural portions of northern Illinois and southern Wisconsin that are visible, what really strikes the eye are the abandoned warehouses and old, long dead factories. Graffiti "artists" have tagged anything.