Next departures for Chicago to Portland on November 20
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Portland Curbside Bus Stop
CheapestFastest
Bus
537-517 W. Jackson Blvd
Portland Curbside Bus Stop
No tags
Next departures for Chicago to Portland on November 21
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Portland Curbside Bus Stop
CheapestFastest
Bus
537-517 W. Jackson Blvd
Portland Curbside Bus Stop
No tags
Next departures for Chicago to Portland on November 22
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Portland Curbside Bus Stop
CheapestFastest
Bus
537-517 W. Jackson Blvd
Portland Curbside Bus Stop
No tags
Next departures for Chicago to Portland on November 23
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Portland Curbside Bus Stop
CheapestFastest
Bus
537-517 W. Jackson Blvd
Portland Curbside Bus Stop
No tags
Next departures for Chicago to Portland on November 24
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Portland Curbside Bus Stop
CheapestFastest
Bus
537-517 W. Jackson Blvd
Portland Curbside Bus Stop
No tags
Next departures for Chicago to Portland on November 25
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Portland Curbside Bus Stop
CheapestFastest
Bus
537-517 W. Jackson Blvd
Portland Curbside Bus Stop
No tags
Next departures for Chicago to Portland on November 26
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Chicago 95Th & Dan Ryan
Portland Curbside Bus Stop
CheapestFastest
Bus
537-517 W. Jackson Blvd
Portland Curbside Bus Stop
No tags
Last refresh of the prices: Today at 10:25 AM CST.
Compare 2 ways to go from Chicago to Portland
We recommend taking the train
Among the sustainable travel choices, the train stands out as the good way to reach Portland. The journey takes about 2 days, 4 hours 40 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.
Greyhound Chicago Portland recent customer reviews
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.
7418 NW Station Way (across street), Portland, OR 97209, USA
Frequently asked questions about traveling from Chicago to Portland, OR by bus
What is the distance between Chicago and Portland?
The distance between the two cities is 1753 miles (2827 km).
What are the departure and arrival stations when taking the bus from Chicago to Portland?
If you're headed to Portland from Chicago, chances are that your bus will depart from Downtown Greyhound Station and arrive at Portland Union Station. These are the main departure and arrival 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 Portland?
Once in Portland, you can start exploring the city and discover its surroundings. The top sights and things to do are Portland Saturday Market, Lan Su Chinese Garden, Forest Park, Breweries and Portland Art Museum.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/17
$530
11/18
$479
Today
$561
11/20
$517
11/21
$410
11/22
$314
11/23
$364
11/24
$440
The cheapest trip from Chicago to Portland, OR was searched and found on Nov 22, 2025 with a price of $314
To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Chicago to Portland, OR, as early as possible.
You can expect to pay from $314 to $561 for a bus ticket from Chicago to Portland, OR based on the last 2 days. You can expect to find the cheapest price for the trip at $314 which is on 2025-11-22.
What's the cheapest way to go from Chicago to Portland, OR?
The bus is the cheapest travel choice for this destination
The cheapest trip from Chicago to Portland, OR was searched and found on Nov 22, 2025 with a price of $314
The bus is the cheapest travel choice for this destination
