How to Book Train Travel From Chicago To Portland. Following the Lewis and Clark trail, Amtrak's Empire Builder offers about 46 hours of scenic train travel from Chicago to Portland. The final leg of the trip passes Mt. Hood and Beacon Rock as the train pulls into Portland's Union Station.
Book Train Travel from Chicago to Portland
Aim to book the #27 train, which is the direct route from Chicago to Portland. Otherwise you'll be switching trains in the wee hours and adding a couple hours to your trip.
Reserve your seats online or by calling an Amtrak agent up to 11 months in advance. All passengers must have a ticket before boarding in Chicago. The fares are lower when travel is booked early.
Check Amtrak's weekly online specials. Savings during non-peak times (mid-October to late May) can be up to 90 percent off published fares.
Upgrade to sleeper accommodations. There are 4 types of rooms available on the Superliner train, which sleep 2 to 6 people. The roomettes and family bedrooms do not have a private bathroom.
Pass the Time aboard the Train
Wear loose clothing and comfortable shoes. Two days of travel from Chicago to Portland can wear anyone down. You'll want to pass time taking catnaps and exploring the train.
Buy Park Place. Finding ways to pass the time can be difficult, so grab one of the board games, such as Monopoly, that Amtrak loans to passengers
Make some friends. Spend time in the lounge meeting some of the interesting people on board the train.
Catch the Scenery from the Train
Keep your eyes out for Glacier National Park as the sun goes down on the second day. The beautiful forest and deep-cut gorges are a perfect ending to the day.
Wake up to the Columbia River Gorge. The last few hours aboard are spent following the river canyon to Portland.
Don't miss Mt. Hood. The iconic mountain makes a brief appearance just before you enter the urban area of Portland.