Next departures for Portland to Chicago on November 13
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
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 14
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
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 15
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
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 16
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
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 17
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
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
FlixBus + Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
No tags
Next departures for Portland to Chicago on November 18
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
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
FlixBus + Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
No tags
Next departures for Portland to Chicago on November 19
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
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
FlixBus + Greyhound Lines, Inc. + FlixBus
Bus
Portland Curbside Bus Stop
Chicago 95Th & Dan Ryan
No tags
Last refresh of the prices: Yesterday at 7:35 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 the good way to reach Chicago. The journey takes about 2 days, 4 hours 5 minutes and with fares starting at just $133, it presents an excellent value for a comfortable ride.
Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.
Based on 5582 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $565
Flixbus is a European bus operator that offers intercity and bus travel in over 38 countries. Known for their easy-to-spot lime green buses and for offering affordable transportation between cities in Europe and the Americas, Flixbus is a good option for those looking for an affordable, reliable bus company. In their buses, you'll find free WiFi, bathrooms, and power outlets. You can also pay extra to choose your seat and get extra legroom, or even buy a snack or drink onboard directly from the driver. You can reschedule your ticket for a small fee, which varies from $1 to $5, depending on how close you are to the departure date.
Frequently asked questions about traveling from Portland, OR to Chicago by bus
What is the travel distance from Portland to Chicago?
The distance separating Portland and Chicago is 1753 miles (2827 km).
What are the departure and arrival stations when taking the bus from Portland to Chicago?
The majority of buses traveling from Portland to Chicago start their journey at Portland Union Station and wind up at Downtown Greyhound Station. These are the most popular pick-up and drop-off locations on this route, but you could find others that could be a better fit for your travel plans.
What are the best sights and things to do in Chicago?
Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Cloud Gate, Grant Park, Brookfield Zoo, Lincoln Park Conservatory and Navy Pier.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/10
$383
11/11
$331
Today
$353
11/13
$428
11/14
$237
11/15
$182
11/16
$261
11/17
$256
The cheapest trip from Portland, OR to Chicago was searched and found on Nov 15, 2025 with a price of $182
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 $182 to $495 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 $182 which is on 2025-11-15.
What's the cheapest way to go from Portland, OR to Chicago?
The bus is the cheapest travel choice for this destination