Travel from Portland to Chicago

Train, bus or fly from Portland to Chicago?

Southwest Airlines and Delta fly from Portland to Chicago hourly. Alternatively, Amtrak operates a train from Portland to Chicago once daily. Tickets cost $270 - $850 and the journey takes 45 h 10 min.

Book transport from Portland to Chicago

Travel Guides

Want to know more about US trains?Rome2rio has everything you need to know about travelling with Amtrak
Need to know: GreyhoundRome2rio’s guide on the bus operator has all the information you need

How to get from Portland to Chicago

From Skidmore Fountain station tram to Portland airport, fly to Chicago Midway airport, then subway to Chicago. 5 h 56 min $236. From Skidmore Fountain station tram to Portland airport, fly to Chicago O'Hare airport, then subway to Chicago. 6 h 11 min $187. From Skidmore Fountain station tram to Portland airport, fly to South Bend airport, then train to Chicago. 10 h 15 min $615. From Skidmore Fountain station tram to Portland airport, fly to Milwaukee airport, bus to Milwaukee Intermodal Station Amtrak, then train to Chicago. 8 h 37 min $215. From Portland Union Station Amtrak train to Chicago Union Station Amtrak. 45 h 10 min $597. From Portland, OR bus to Denver, CO, bus to Des Moines, IA, then bus to Chicago, IL. 2 days 3 h $288. From Portland drive to Chicago. 33 h 3 min $255.