Next departures for Portland to Chicago on November 20
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 for Portland to Chicago on November 21
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 for Portland to Chicago on November 22
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 for Portland to Chicago on November 23
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 for Portland to Chicago on November 25
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 for Portland to Chicago on November 26
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 5:20 PM PST.
Compare 2 ways to go 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 $191, 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 WiFi. Greyhound ticket prices on this trip start at $151
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 WiFi. Amtrak ticket prices on this trip start at $810
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 WiFi. FlixBus ticket prices on this trip start at $204
Frequently asked questions about travelling from Portland, OR to Chicago by bus
What is the travel distance from Portland to Chicago?
The distance between Portland and Chicago is around 2827 km (1753 miles).
What are the departure and arrival locations for buses traveling from Portland to Chicago?
Buses traveling this route start their trip at Portland Union Station, in Portland, and end it at Downtown Greyhound Station, in Chicago.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11-16
$546
11-17
$513
Today
$465
11-19
$619
11-20
$784
11-21
$537
11-22
$444
11-23
$515
The cheapest trip from Portland, OR to Chicago was searched and found on Nov 22, 2025 with a price of $444
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 $444 to $857 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 $444 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 Nov 22, 2025 with a price of $444
The bus is the cheapest travel choice for this destination
