Cheap Flights From Chicago, Illinois (CHI) To Portland, Maine (PWM) - No Deals

Flight from Chicago to Portland (MDW-PWM)

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There are approximately 5 flights covering the route from Midway Airport in Chicago to Portland International Jetport in Portland, provided by as many as 1 airlines.

The following airlines often offer cheap flights from Chicago to Portland:

Delta Air Lines

As an alternative to flying from Chicago, you may also want to try searching for cheap flights from Chicago (ORD).