There are 7 ways to get from Chicago to Oregon by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 31m$256–1,108Fly Chicago O'Hare International Airport to Portland International Airport
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Portland International Airport (PDX)plane ORD - PDX
6h 54m$166–758Train (Amtrak)
- Take the train from Chicago Union Station to Portlandtrain Empire Builder
46h 12m$600–1,400Bus
- Take the bus from Chicago Bus Station to Denver Union Stationbus
- Take the bus from Denver Union Station to Pasco Bus Stopbus
- Take the bus from Pasco Bus Stop to Portland Curbside Bus Stopbus
2d 2h$386–742Drive 2,077 mi
- Drive from Chicago to Portlandcar 2,077 mi
33h 44m$380–548Fly Chicago O'Hare International Airport to Mahlon Sweet Field Airport
- Fly from Chicago O'Hare International Airport (ORD) to Mahlon Sweet Field Airport (EUG)plane ORD - EUG
6h 47m$242–995Fly 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 6m$362–1,545
Chicago to Oregon by train (Amtrak)
Questions & Answers
The cheapest way to get from Chicago to Oregon is to fly which costs $160 - $800 and takes 6h 54m.
The fastest way to get from Chicago to Oregon is to fly which takes 6h 31m and costs $250 - $1,200.
No, there is no direct bus from Chicago station to Oregon. However, there are services departing from Chicago Bus Station and arriving at Portland Curbside Bus Stop via Denver Union Station and Pasco Bus Stop. The journey, including transfers, takes approximately 2 days 2h.
Yes, there is a direct train departing from Chicago Union Station station and arriving at Portland. Services depart once daily, and operate every day. The journey takes approximately 46h 12m.
The distance between Chicago and Oregon is 1779 miles. The road distance is 2089.1 miles.
The best way to get from Chicago to Oregon without a car is to train which takes 46h 12m and costs $600 - $1,400.
It takes approximately 6h 31m to get from Chicago to Oregon, including transfers.
Chicago to Oregon bus services, operated by Greyhound USA, depart from Chicago Bus Station.
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 31m and costs $250 - $1,200. Alternatively, you can train, which costs $600 - $1,400 and takes 46h 12m, you could also bus, which costs $380 - $750 and takes 2 days 2h.
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) every 4 hours. Alternatively, Amtrak operates a train from Chicago Union Station to Portland once daily. Tickets cost $600–1,400 and the journey takes 46h 12m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Portland International Airport
- Ave. Duration
- 4h 18m
- When
- Every day
- Estimated price
- $250–1,100
Flights from Chicago Midway International Airport to Portland International Airport via Denver
- Ave. Duration
- 6h 38m
- When
- Every day
- Estimated price
- $260–1,200
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Denver
- Ave. Duration
- 7h 28m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $330–1,500
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Las Vegas
- Ave. Duration
- 7h 58m
- When
- Every day
- Estimated price
- $390–1,600
Flights from Chicago Midway International Airport to Mahlon Sweet Field Airport via Sacramento
- Ave. Duration
- 13h 17m
- When
- Tuesday to Saturday
- Estimated price
- $380–1,600
- Website
- united.com
Flights from Chicago O'Hare International Airport to Portland International Airport
- Ave. Duration
- 4h 31m
- When
- Every day
- Estimated price
- $160–750
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport
- Ave. Duration
- 4h 44m
- When
- Every day
- Estimated price
- $210–950
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Denver
- Ave. Duration
- 7h 30m
- When
- Every day
- Estimated price
- $220–1,000
- Website
- alaskaair.com
Flights from Chicago O'Hare International Airport to Portland International Airport
- Ave. Duration
- 4h 30m
- When
- Every day
- Estimated price
- $160–750
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Portland International Airport
- Ave. Duration
- 6h 37m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $220–950
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Seattle
- Ave. Duration
- 7h 24m
- When
- Every day
- Estimated price
- $230–1,000
- Website
- delta.com
Flights from Chicago Midway International Airport to Portland International Airport via Minneapolis
- Ave. Duration
- 8h 18m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $250–1,100
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Salt Lake City
- Ave. Duration
- 7h 31m
- When
- Saturday
- Estimated price
- $220–1,000
Flights from Chicago O'Hare International Airport to Mahlon Sweet Field Airport via Seattle
- Ave. Duration
- 7h 58m
- When
- Every day
- Estimated price
- $230–1,000
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Portland International Airport
- Ave. Duration
- 4h 24m
- When
- Every day
- Estimated price
- $160–750
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
- Once daily
- Estimated price
- $600–1,400
- Website
- https://www.amtrak.com/home.html
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Chicago Bus Station to Denver Union Station
- Ave. Duration
- 21h 35m
- Frequency
- Once daily
- Estimated price
- $160–330
- Website
- https://www.greyhound.com/
Bus from Denver Union Station to Pasco Bus Stop
- Ave. Duration
- 22h 35m
- Frequency
- Once daily
- Estimated price
- $190–370
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Pasco Bus Stop to Portland Curbside Bus Stop
- Ave. Duration
- 4h
- Frequency
- Once daily
- Estimated price
- $28–50
- Schedules at
- flixbus.com
Want to know more about travelling around United States
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More Questions & Answers
Chicago to Oregon bus services, operated by Greyhound USA, arrive at Denver Union Station.
Oregon is 2h behind Chicago. It is currently 2:52 AM in Chicago and 12:52 AM in Oregon.
Chicago to Oregon train services, operated by Amtrak, arrive at Portland station.
Yes, the driving distance between Chicago to Oregon is 2089 miles. It takes approximately 33h 44m to drive from Chicago to Oregon.
Book your Chicago to Oregon train tickets online with Omio.
Book your Chicago to Oregon bus tickets online with Omio and FlixBus.
There are 787+ hotels available in Oregon.







