There are 5 ways to get from Portland to Chicago 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 Midway International Airport
best- Fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW)PDX - MDW
6h 7m$175–808Train (Amtrak)
- Take the train from Portland to Chicago Union StationEmpire Builder
46h$240–1,800Drive 2,077.3 mi
- Drive from Portland to Chicago2,077.3 mi
33h 24m$380–548Fly Portland International Airport to Chicago O'Hare International Airport
- Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)PDX - ORD
6h 19m$245–498Train 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 32m$201–784
Portland to Chicago by train (Amtrak)
Questions & Answers
The cheapest way to get from Portland to Chicago is to fly which costs $240 - $500 and takes 6h 19m.
The fastest way to get from Portland to Chicago is to fly which takes 6h 7m and costs $170 - $850.
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 is 1779 miles. The road distance is 2089.4 miles.
The best way to get from Portland to Chicago without a car is to train which takes 46h and costs $240 - $1,800.
It takes approximately 6h 7m to get from Portland to Chicago, including transfers.
Portland to Chicago train services, operated by Amtrak, depart from Portland station.
The best way to get from Portland to Chicago is to fly which takes 6h 7m and costs $170 - $850. Alternatively, you can train, which costs $240 - $1,800 and takes 46h.
Chicago is 2h ahead of Portland. It is currently 12:39 AM in Portland and 2:39 AM in Chicago.
Portland to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
What companies run services between Portland, OR, USA and Chicago, IL, USA?
Southwest Airlines flies from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) 3 times a day. Alternatively, Amtrak operates a train from Portland to Chicago Union Station twice daily. Tickets cost $240–1,800 and the journey takes 46h.
- Website
- southwest.com
Flights from Portland International Airport to Chicago Midway International Airport
- Ave. Duration
- 3h 55m
- When
- Every day
- Estimated price
- $170–800
Flights from Portland International Airport to Chicago Midway International Airport via Denver
- Ave. Duration
- 6h 30m
- When
- Every day
- Estimated price
- $180–800
Flights from Portland International Airport to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 7h 10m
- When
- Saturday
- Estimated price
- $190–850
Flights from Portland International Airport to Chicago Midway International Airport via Kansas City
- Ave. Duration
- 7h 20m
- When
- Saturday
- Estimated price
- $180–800
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Las Vegas
- Ave. Duration
- 7h
- When
- Saturday
- Estimated price
- $180–800
- Website
- united.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 3m
- When
- Every day
- Estimated price
- $130–600
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
- 7h 3m
- When
- Every day
- Estimated price
- $160–700
- Website
- alaskaair.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 5m
- When
- Every day
- Estimated price
- $130–600
Flights from Portland International Airport to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 6h 5m
- When
- Monday, Tuesday, Wednesday, Friday, and Sunday
- Estimated price
- $130–600
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Seattle
- Ave. Duration
- 7h 28m
- When
- Every day
- Estimated price
- $160–700
- Website
- delta.com
Flights from Portland International Airport to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 7h 12m
- 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
- Every day
- Estimated price
- $160–700
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Salt Lake City
- Ave. Duration
- 6h 54m
- When
- Every day
- Estimated price
- $160–700
- Website
- aa.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 22m
- When
- Every day
- Estimated price
- $130–600
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Phoenix
- Ave. Duration
- 6h 51m
- When
- Monday, Tuesday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $190–800
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
- $240–1,800
- Website
- https://www.amtrak.com/home.html
Train from Portland to Eugene
- Ave. Duration
- 2h 38m
- Frequency
- 3 times a day
- Estimated price
- $19–40
- Website
- https://www.amtrak.com/home.html
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More Questions & Answers
Yes, the driving distance between Portland to Chicago is 2089 miles. It takes approximately 33h 24m to drive from Portland to Chicago.
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