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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From $249 / RT details

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Cheap Portland airfares from $249/RT are provided by Cheapoair.com. Outbound flight is leaving on 08/15/2024, 09:04 pm from Chicago Midway (MDW) airport and arrives at Portland Intl (PWM) at 04:24 pm. The flight time is 19 hours and 20 minutes. The Returning flight departes on 08/29/2024, 01:58 pm (other return dates are also available). Date posted: 02 Jul 2024

Price evolution for flights From Chicago To Portland, Maine

Price overview for flights from Chicago to Portland, Maine

Recent Deals on Flights from Chicago to Portland, Maine:Roundtrip / Oneway

  • $249Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Portland, ME (PWM)08/15/202409:04 pm
    Portland, ME (PWM)Chicago, IL (MDW)08/29/202401:58 pm
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  • $82Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Portland, ME (PWM)08/10/202411:51 am
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  • $94Frontier Airlines flight Frontier Airlines 
    FromToDepartureTime
    Chicago, IL (MDW)Portland, ME (PWM)08/17/202411:51 am
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  • $204Sun Country Airlines flight Sun Country Airlines 
    FromToDepartureTime
    Chicago, IL (ORD)Portland, ME (PWM)08/02/202408:05 pm
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