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.

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.

Portland (PWM) to Chicago (ORD) flight schedule. The monthly calendar shows every direct flight departure from Portland International Jetport (PWM) with all airlines. Click on a date to see a …

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

The cheapest way to get from Chicago to Portland costs only $170, and the quickest way takes just 4 hours. Find the travel option that best suits you.

What is the cheapest flight from Chicago O'Hare Intl Airport to Portland? In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Portland was $55 for a one-way …

What is the cheapest flight from Portland to Chicago O'Hare Intl Airport? In the last 3 days, the lowest price for a flight from Portland to Chicago O'Hare Intl Airport was $63 for a one-way …

The journey from Portland to Chicago can take as little as 30 hours 20 minutes and starts from as little as $126.98. The earliest bus leaves at 1:45 pm . Greyhound provides daily buses …

Fly one-way from Chicago (O'Hare) to Portland, ME, starting at $125. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

There are 7 ways to get from Chicago to Maine by plane, train, bus, or car. Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's …