Cheap Flights from Portland (PDX) to Chicago (ORD) start at $60 for one-way and $120 for round trip. Earn your airline miles on top of our rewards!

Our data shows that the cheapest route for a return flight from Portland to Chicago cost $238 and was between Portland (PDX) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route.

Find United Airlines cheap flights from Portland, OR to Chicago. Enjoy a Portland, OR to Chicago modern flight experience in premium cabins with Wi-Fi.

Flights from Portland to Chicago. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Portland to Chicago.

Fly one-way from Portland, OR, to Chicago (Midway) starting at $165. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

There are 5 ways to get from Portland to Chicago by plane, bus, night bus, train, or car. Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

Detailed flight information from Portland PDX to Chicago ORD. See all airline(s) with scheduled flights and weekly timetables up to 9 months ahead. Flightnumbers and complete route information.

Each day, there are between 2 and 4 nonstop flights that take off from Portland and land in Chicago O'Hare Intl Airport, with an average flight time of 4h 01m. The most common departure time is 7:00 am and most flights take off in the morning.

3 days ago · All direct (non-stop) flights from Portland to Chicago. See airlines, aircrafts, flight time and distance, flight schedules and timetables.

Jan 17, 2025 · Explore the most affordable flight options available from Portland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 17, 2025.