Next departures from Portland to Chicago on 20 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
Cheapest
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
No tags
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
Next departures from Portland to Chicago on 21 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
Cheapest
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
No tags
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
Next departures from Portland to Chicago on 22 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
Cheapest
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
No tags
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
Next departures from Portland to Chicago on 23 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
Cheapest
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
No tags
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
Next departures from Portland to Chicago on 25 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
CheapestFastest
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
No tags
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
No tags
Next departures from Portland to Chicago on 26 November
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
CheapestFastest
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
No tags
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
No tags
Last refresh of the prices: Today at 17:20 PST.
Compare 2 ways to travel from Portland to Chicago
We recommend taking the train
Among the sustainable travel choices, the train stands out as a good way to reach Chicago. The journey takes about 2 days, 4 hours 5 minutes and with fares starting at just £104, it presents an excellent value for a comfortable ride.
Based on 87382 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the temperature but often complained with the Wi-Fi. Greyhound ticket prices on this trip start at £83
Based on 5593 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at £441
Based on 11371 reviews, the company was rated 3.5 stars on Busbud. Travellers were especially satisfied with the ticket access and the staff but often complained with the Wi-Fi. FlixBus ticket prices on this trip start at £111
Frequently asked questions about travelling by bus from Portland, OR to Chicago
How far is Chicago from Portland by coach?
The distance between Portland and Chicago by coach is approximately 1753 miles (2827 km).
Is there a way to reach Chicago from Portland without flying?
You can choose the coach to travel this route. Choosing the coach guarantees a comfortable and sustainable travel experience, allowing you to admire the views on your way to your destination. You also have the option of utilising carpooling services.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
16/11
£297
17/11
£279
Today
£253
19/11
£337
20/11
£426
21/11
£292
22/11
£241
23/11
£280
The cheapest trip from Portland, OR to Chicago was searched and found on 22 Nov 2025 with a price of £241
To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Portland, OR to Chicago as early as possible.
You can expect to pay from £241 to £466 for a bus ticket from Portland, OR to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at £241, which is on 2025-11-22.
What's the cheapest way to go from Portland, OR to Chicago?
The bus is the cheapest travel choice for this destination
The cheapest trip from Portland, OR to Chicago was searched and found on 22 Nov 2025 with a price of £241
The bus is the cheapest travel choice for this destination
