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 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.

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

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

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.

Fly to Portland, Maine, with United Airlines from over 200 airports within the United States and an additional 100 airports internationally. Dive into local history at the Tate House Mansion, …

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 …

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

The cheapest ticket to Maine from Chicago found in the last 72 hours was $45 one-way, and $100 round-trip. The most popular route is from Chicago to Portland , and the cheapest round-trip …

Find cheap fares from Chicago, IL (MDW) to Portland, ME (PWM) with Frontier Airlines. Enjoy unlimited savings all year with the Discount Den℠!