There are 6 ways to get from Chicago to Oregon by plane, train (Amtrak), or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago Midway International Airport to Portland International Airport
best- Fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX)plane MDW - PDX
6h 40m$236–1,108Fly Chicago O'Hare International Airport to Mahlon Sweet Field Airport
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Mahlon Sweet Field Airport (EUG)plane ORD - EUG
6h 46m$142–595Train (Amtrak)
- Take the train from Chicago Union Station to Portlandtrain Empire Builder
46h 12m$170–1,200Drive 2,077 mi
- Drive from Chicago to Portlandcar 2,077 mi
33h 43m$380–548Fly Chicago O'Hare International Airport to Portland International Airport
- Fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX)plane ORD - PDX
7h 4m$176–808Fly Chicago Midway International Airport to Mahlon Sweet Field Airport
- Fly from Chicago Midway International Airport (MDW) to Mahlon Sweet Field Airport (EUG)plane MDW - EUG
8h 43m$192–795
Chicago to Oregon by train (Amtrak)
Questions & Answers
The cheapest way to get from Chicago to Oregon is to fly which costs $140 - $600 and takes 6h 46m.
The fastest way to get from Chicago to Oregon is to fly which takes 6h 40m and costs $230 - $1,200.
Yes, there is a direct train departing from Chicago Union Station station and arriving at Portland. Services depart twice daily, and operate every day. The journey takes approximately 46h 12m.
The distance between Chicago and Oregon is 1779 miles. The road distance is 2089.2 miles.
The best way to get from Chicago to Oregon without a car is to train which takes 46h 12m and costs $170 - $1,200.
It takes approximately 6h 40m to get from Chicago to Oregon, including transfers.
Chicago to Oregon train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Oregon is to fly which takes 6h 40m and costs $230 - $1,200. Alternatively, you can train, which costs $170 - $1,200 and takes 46h 12m.
Oregon is 2h behind Chicago. It is currently 1:58 AM in Chicago and 11:58 PM in Oregon.
Chicago to Oregon train services, operated by Amtrak, arrive at Portland station.
What companies run services between Chicago, IL, USA and Oregon, USA?
Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Portland International Airport (PDX) 3 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Portland twice daily. Tickets cost $170–1,200 and the journey takes 46h 12m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Portland International Airport
- Ave. Duration
- 4h 33m
- When
- Every day
- Estimated price
- $230–1,100
Flights from Chicago Midway International Airport to Portland International Airport via Kansas City
- Ave. Duration
- 8h 45m
- When
- Saturday
- Estimated price
- $250–1,100
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Oakland
- Ave. Duration
- 7h 15m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $190–850
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Las Vegas
- Ave. Duration
- 7h 20m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $180–800
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Denver
- Ave. Duration
- 7h 50m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $160–750
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via San Jose
- Ave. Duration
- 10h
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $190–850
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Sacramento
- Ave. Duration
- 13h 40m
- When
- Every day
- Estimated price
- $180–800
- Website
- united.com
Flights from Chicago O'Hare International Airport to Portland International Airport
- Ave. Duration
- 4h 43m
- When
- Every day
- Estimated price
- $170–800
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport
- Ave. Duration
- 4h 43m
- When
- Every day
- Estimated price
- $110–550
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Denver
- Ave. Duration
- 7h 39m
- When
- Every day
- Estimated price
- $120–550
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Denver
- Ave. Duration
- 6h 57m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $160–750
- Website
- delta.com
Flights from Chicago Midway International Airport to Portland International Airport via Minneapolis
- Ave. Duration
- 9h 4m
- When
- Every day
- Estimated price
- $230–1,100
Flights from Chicago O'Hare International Airport to Portland International Airport via Minneapolis
- Ave. Duration
- 7h 48m
- When
- Every day
- Estimated price
- $170–800
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Salt Lake City
- Ave. Duration
- 7h 19m
- When
- Every day
- Estimated price
- $120–550
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Seattle
- Ave. Duration
- 8h 49m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $120–550
- Website
- alaskaair.com
Flights from Chicago O'Hare International Airport to Portland International Airport
- Ave. Duration
- 4h 42m
- When
- Monday, Tuesday, Thursday, Friday, and Sunday
- Estimated price
- $170–800
Flights from Chicago O'Hare International Airport to Portland International Airport via Bozeman
- Ave. Duration
- 6h 19m
- When
- Saturday
- Estimated price
- $170–800
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Seattle
- Ave. Duration
- 7h 48m
- When
- Every day
- Estimated price
- $120–550
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Seattle
- Ave. Duration
- 7h 3m
- When
- Every day
- Estimated price
- $170–750
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Portland International Airport
- Ave. Duration
- 4h 33m
- When
- Every day
- Estimated price
- $170–800
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Portland
- Ave. Duration
- 46h 12m
- Frequency
- Twice daily
- Estimated price
- $170–1,200
- Website
- https://www.amtrak.com/home.html
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
More Questions & Answers
Yes, the driving distance between Chicago to Oregon is 2089 miles. It takes approximately 33h 43m to drive from Chicago to Oregon.
Book your Chicago to Oregon train tickets online with Omio.
There are 765+ hotels available in Oregon.