Fly one-way from Portland, ME, to Chicago (O'Hare) starting at $109. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

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

The cheapest round-trip flight from Portland to Chicago starts at $110 from Thu, Feb 20 to Wed, Feb 26. The cheapest one-way flight starts at $55 and departs on Tue, Feb 25.

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

Are you searching for American Airlines flights from Portland, ME to Chicago? Find the best selections and fly in style.

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

Find flights to Chicago O'Hare Airport from $61. Fly from Portland on Frontier, JetBlue, Delta and more. Search for Chicago O'Hare Airport flights on KAYAK now to find the best deal.

Are you searching for American Airlines flights from Chicago to Portland, ME? Find the best selections and fly in style.

The best one-way flight to Chicago from Portland, Maine in the past 72 hours is $95. The best round-trip flight deal from Portland, Maine to Chicago found on momondo in the last 72 hours …

Jan 23, 2025 · Find airfare and ticket deals for cheap flights from Portland, ME to Chicago. Search flight deals from various travel partners with one click at $61.