Cheap flights from Chicago to Portland, Maine
Travel > North America > United States > Chicago to Portland, Maine flights
Check our current prices for flights from Chicago to Portland, Maine. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to Portland, Maine, you will need to run a search below.
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Cheap Portland airfares from $188/RT are provided by Cheapoair.com. Outbound flight is leaving on 01/24/2024, 08:35 pm from Chicago Midway (MDW) airport and arrives at Portland Intl (PWM) at 07:31 pm. The flight time is 22 hours and 56 minutes. The Returning flight departes on 02/07/2024, 08:31 pm (other return dates are also available). Date posted: 20 Sep 2023
Price evolution for flights From Chicago To Portland, Maine

Recent Deals on Flights from Chicago to Portland, Maine:Roundtrip / Oneway
- $188
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Portland, ME (PWM) 01/24/2024 08:35 pm Portland, ME (PWM) Chicago, IL (MDW) 02/07/2024 08:31 pm - $248
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Portland, ME (PWM) 01/31/2024 05:00 pm Portland, ME (PWM) Chicago, IL (ORD) 02/13/2024 08:31 pm - We are sorry but currently there are no oneway offers for flights from Chicago to Portland, Maine.
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