There are 5 ways to get from Portland to Chicago Loop by plane, train (Amtrak), 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.
Fly Portland International Airport to Chicago O'Hare International Airport
best- Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)PDX - ORD
6h 9m$100–498Train (Amtrak)
- Take the train from Portland to Chicago Union StationEmpire Builder
46h$280–550Drive 2,076.6 mi
- Drive from Portland to Chicago Loop2,076.6 mi
33h 22m$379–548Fly Portland International Airport to Chicago Midway International Airport
- Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)PDX - MDW
6h 9m$185–858Train to Mahlon Sweet Field Airport, fly to Chicago O'Hare International Airport
- Take the train from Portland to Eugene
- Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)EUG - ORD
8h 29m$199–775
Portland to Chicago Loop by train (Amtrak)
Questions & Answers
The cheapest way to get from Portland to Chicago Loop is to fly which costs $100 - $500 and takes 6h 9m.
The fastest way to get from Portland to Chicago Loop is to fly which takes 6h 9m and costs $100 - $500.
Yes, there is a direct train departing from Portland and arriving at Chicago Union Station station. Services depart twice daily, and operate every day. The journey takes approximately 46h.
The distance between Portland and Chicago Loop is 1773 miles. The road distance is 2088.7 miles.
The best way to get from Portland to Chicago Loop without a car is to train which takes 46h and costs $280 - $550.
It takes approximately 6h 9m to get from Portland to Chicago Loop, including transfers.
Portland to Chicago Loop train services, operated by Amtrak, depart from Portland station.
The best way to get from Portland to Chicago Loop is to fly which takes 6h 9m and costs $100 - $500. Alternatively, you can train, which costs $280 - $550 and takes 46h.
Chicago Loop is 2h ahead of Portland. It is currently 4:49 AM in Portland and 6:49 AM in Chicago Loop.
Portland to Chicago Loop train services, operated by Amtrak, arrive at Chicago Union Station.
What companies run services between Portland, OR, USA and Chicago Loop, IL, USA?
American Airlines, Alaska Airlines, Inc., and two other airlines fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD) every 3 hours. Alternatively, Amtrak operates a train from Portland to Chicago Union Station twice daily. Tickets cost $280–550 and the journey takes 46h.
- Website
- united.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 59m
- When
- Every day
- Estimated price
- $120–600
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport
- Ave. Duration
- 3h 52m
- When
- Every day
- Estimated price
- $150–700
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Denver
- Ave. Duration
- 6h 57m
- When
- Every day
- Estimated price
- $150–750
- Website
- delta.com
Flights from Portland International Airport to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 6h 44m
- When
- Every day
- Estimated price
- $120–600
Flights from Portland International Airport to Chicago Midway International Airport via Minneapolis
- Ave. Duration
- 6h 26m
- When
- Every day
- Estimated price
- $180–850
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Salt Lake City
- Ave. Duration
- 6h 51m
- When
- Every day
- Estimated price
- $150–750
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Seattle
- Ave. Duration
- 8h 18m
- When
- Every day
- Estimated price
- $160–750
- Website
- alaskaair.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 5m
- When
- Every day
- Estimated price
- $120–600
Flights from Portland International Airport to Chicago O'Hare International Airport via Kansas City
- Ave. Duration
- 8h 27m
- When
- Every day
- Estimated price
- $130–600
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Seattle
- Ave. Duration
- 6h 24m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $160–750
- Website
- southwest.com
Flights from Portland International Airport to Chicago Midway International Airport
- Ave. Duration
- 3h 55m
- When
- Every day
- Estimated price
- $180–850
Flights from Portland International Airport to Chicago Midway International Airport via Denver
- Ave. Duration
- 5h 45m
- When
- Monday to Thursday
- Estimated price
- $190–900
Flights from Portland International Airport to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 8h 35m
- When
- Saturday
- Estimated price
- $190–900
- Website
- aa.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 12m
- When
- Every day
- Estimated price
- $120–600
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Phoenix
- Ave. Duration
- 7h 29m
- When
- Every day
- Estimated price
- $190–850
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Portland to Chicago Union Station
- Ave. Duration
- 46h
- Frequency
- Twice daily
- Estimated price
- $280–550
- Website
- https://www.amtrak.com/home.html
Train from Portland to Eugene
- Ave. Duration
- 2h 38m
- Frequency
- 3 times a day
- Estimated price
- $17–30
- Website
- https://www.amtrak.com/home.html
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More Questions & Answers
Yes, the driving distance between Portland to Chicago Loop is 2089 miles. It takes approximately 33h 22m to drive from Portland to Chicago Loop.
Book your Portland to Chicago Loop train tickets online with Omio.
There are 978+ hotels available in Chicago Loop.