Next departures for Portland to Chicago on December 15
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
Downtown Greyhound Station
CheapestFastest
FlixBus + Greyhound Lines, Inc.
Bus
Portland Curbside Bus Stop
537-517 W. Jackson Blvd
No tags
Next departures for Portland to Chicago on December 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
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 December 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
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 December 18
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 December 19
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 December 20
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 December 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 December 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
Last refresh of the prices: Today at 4:30 AM 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 5647 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
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the bus ticket from Portland to Chicago?
The cheapest bus tickets from Portland to Chicago start from $106. The average price for this route is around $226. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Portland to Chicago?
The average bus trip duration from Portland to Chicago is 3d 6h, covering a distance of 1751 miles (2823 km). The quickest bus can get you there in 1d 22h and is operated by Amtrak.
Which bus companies service the Portland to Chicago route?
Several major bus companies operate on this route with 8 buses available per day, including services from Greyhound, Amtrak, FlixBus.
What is the earliest and latest departure time for the bus from Portland to Chicago?
The earliest bus departs from Portland to Chicago at 2:00am. And the latest bus departs at 8:00pm.
What are the CO₂ emissions for the bus trip from Portland to Chicago?
A bus trip from Portland to Chicago generates an estimated 71 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.
What is the best bus company from Portland to Chicago?
According to Busbud customers, the highest-rated bus company on this route is Amtrak, with an average rating of 4.1 out of 5 stars based on 5627 reviews.
Which bus company has the best Wi-Fi from Portland to Chicago?
Based on reviews on Busbud, the bus company Amtrak has the best Wi-Fi rating with a score of 3.6.
Which bus company has the most timely service from Portland to Chicago?
According to Busbud traveller reviews, the most timely bus company on this route is FlixBus, with a punctuality rating of 3.9 out of 5 stars.
Which bus company has the cleanest buses from Portland to Chicago?
According to Busbud traveller reviews, the bus company with the cleanest buses on this route is Amtrak, with a cleanliness rating of 4.5 out of 5 stars.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
12/12
$374
12/13
$457
Today
$384
12/15
$576
12/16
$644
12/17
$310
12/18
$403
12/19
$399
The cheapest trip from Portland, OR to Chicago was searched and found on Dec 17, 2025 with a price of $310
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 $310 to $729 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 $310 which is on 2025-12-17.
What's the cheapest way to go from Portland, OR to Chicago?
The bus is the cheapest travel choice for this destination