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!

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.

Find flights to Chicago from $41. Fly from Portland on Frontier, Spirit Airlines and more. Search for Chicago flights on KAYAK now to find the best deal.

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.

The best way to get from Portland to Chicago is to fly which takes 6h 1m and costs $100 - $550. Alternatively, you can train, which costs $180 - $600 and takes 46h.

Find flights to Chicago O'Hare Airport from $55. Fly from Portland on Spirit Airlines, Frontier and more. Search for Chicago O'Hare Airport flights on KAYAK now to find the best deal.

Find the best deals on flights from Portland (PDX) to Chicago (CHIA). Compare prices from hundreds of major travel agents and airlines, all in one search.

Jan 27, 2025 · All direct (non-stop) flights from Portland to Chicago. See airlines, aircrafts, flight time and distance, flight schedules and timetables.

Jan 23, 2025 · Find airfare and ticket deals for cheap flights from Portland to Chicago. Search flight deals from various travel partners with one click at $110.

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.