There are 5 ways to get from Hillsboro to Chicago by plane, train (Amtrak), car, or bus
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)plane PDX - MDW
7h 12m$108–461Bus, bus to Mahlon Sweet Field Airport, fly to Chicago O'Hare International Airport
cheapest- Take the bus from Hillsboro - SE 4th btwn Washington & Main to McMinnville Transit Centerbus
- Take the bus from McMinnville to Eugene Airportbus
- Fly from Mahlon Sweet Field Airport (EUG) to Chicago O'Hare International Airport (ORD)plane EUG - ORD
10h 15m$91–385Train (Amtrak)
- Take the train from Portland to Chicago Union Stationtrain Empire Builder
2d$1,203–1,903Drive 2,095.3 mi
- Drive from Hillsboro to Chicagocar 2,095.3 mi
34h 9m$383–553Fly Portland International Airport to Chicago O'Hare International Airport
- Fly from Portland International Airport (PDX) to Chicago O'Hare International Airport (ORD)plane PDX - ORD
7h 28m$178–311
Hillsboro to Chicago by tram, foot, and train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Hillsboro to Chicago is to bus and fly which costs $90 - $390 and takes 10h 15m.
The fastest way to get from Hillsboro to Chicago is to fly which takes 7h 12m and costs $100 - $470.
No, there is no direct train from Hillsboro station to Chicago station. However, there are services departing from Hatfield Government Center station and arriving at Chicago Union Station via Portland. The journey, including transfers, takes approximately 2 days 0h.
The distance between Hillsboro and Chicago is 1798 miles. The road distance is 2107.5 miles.
The best way to get from Hillsboro to Chicago without a car is to train which takes 2 days 0h and costs $1,200 - $1,900.
It takes approximately 7h 12m to get from Hillsboro to Chicago, including transfers.
Hillsboro to Chicago train services, operated by Amtrak, depart from Portland station.
The best way to get from Hillsboro to Chicago is to fly which takes 7h 12m and costs $100 - $470. Alternatively, you can train, which costs $1,200 - $1,900 and takes 2 days 0h.
Chicago is 2h ahead of Hillsboro. It is currently 10:26 AM in Hillsboro and 12:26 PM in Chicago.
Hillsboro to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
What companies run services between Hillsboro, OR, USA and Chicago, IL, USA?
Southwest Airlines and Delta fly from Portland International Airport (PDX) to Chicago Midway International Airport (MDW) 4 times a day. Alternatively, Amtrak operates a train from Portland to Chicago Union Station once daily. Tickets cost $1,200–1,900 and the journey takes 46h.
- Website
- united.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 8m
- When
- Every day
- Estimated price
- $80–350
Flights from Portland International Airport to Chicago O'Hare International Airport via Denver
- Ave. Duration
- 6h 22m
- When
- Every day
- Estimated price
- $85–370
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 12m
- When
- Every day
- Estimated price
- $80–350
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Denver
- Ave. Duration
- 6h 20m
- When
- Every day
- Estimated price
- $80–360
- Website
- southwest.com
Flights from Portland International Airport to Chicago Midway International Airport
- Ave. Duration
- 3h 50m
- When
- Every day
- Estimated price
- $100–450
Flights from Portland International Airport to Chicago Midway International Airport via Denver
- Ave. Duration
- 6h 5m
- When
- Every day
- Estimated price
- $110–470
- Website
- delta.com
Flights from Portland International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 8h 20m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $120–550
Flights from Portland International Airport to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 6h 36m
- When
- Every day
- Estimated price
- $80–360
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Salt Lake City
- Ave. Duration
- 6h 29m
- When
- Every day
- Estimated price
- $80–360
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Seattle
- Ave. Duration
- 8h 54m
- When
- Every day
- Estimated price
- $85–360
- Website
- alaskaair.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 18m
- When
- Every day
- Estimated price
- $210–310
Flights from Mahlon Sweet Field Airport to Chicago O'Hare International Airport via Seattle
- Ave. Duration
- 7h 6m
- When
- Every day
- Estimated price
- $130–550
- Website
- aa.com
Flights from Portland International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 4h 16m
- When
- Every day
- Estimated price
- $80–350
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Portland to Chicago Union Station
- Ave. Duration
- 46h
- Frequency
- Once daily
- Estimated price
- $1,200–1,900
- Website
- Amtrak
- Phone
- +1 503-474-4900
- Website
- Yamhill County Transit
Bus from Hillsboro - SE 4th btwn Washington & Main to McMinnville Transit Center
- Ave. Duration
- 1h 2m
- Frequency
- 3 times a day
- Website
- Yamhill County Transit
- Phone
- +1 541-366-5110
- [email protected]
- Website
- Pacific Crest Bus Lines
Bus from McMinnville to Eugene Airport
- Ave. Duration
- 2h 15m
- Frequency
- 5 times a week
- Estimated price
- $9–30
- Website
- Pacific Crest Bus Lines
Want to know more about travelling around United States
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Booking & Getting There
Yes, the driving distance between Hillsboro to Chicago is 2107 miles. It takes approximately 34h 9m to drive from Hillsboro to Chicago.
There are 1308+ hotels available in Chicago.








