Cheap flights from Chicago to Portland

Travel > North America > United States > Chicago to Portland flights

Check our current prices for flights from Chicago to Portland. 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, you will need to run a search below.

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From $135 / RT details

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Cheap Portland airfares from $135/RT are provided by Cheapoair.com. Outbound flight is leaving on 02/18/2025, 07:05 am from Chicago Midway (MDW) airport and arrives at Portland Intl (PDX) at 12:37 am. The flight time is 17 hours and 32 minutes. The Returning flight departes on 02/24/2025, 06:32 am (other return dates are also available). Date posted: 05 Jan 2025

Price evolution for flights From Chicago To Portland

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

• $135 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Portland, OR (PDX)	02/18/2025	07:05 am
  Portland, OR (PDX)	Chicago, IL (MDW)	02/24/2025	06:32 am

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• $135 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Portland, OR (PDX)	02/18/2025	06:50 am
  Portland, OR (PDX)	Chicago, IL (ORD)	02/24/2025	06:32 am

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• $149 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Portland, OR (PDX)	02/18/2025	07:51 pm
  Portland, OR (PDX)	Chicago, IL (ORD)	02/24/2025	06:32 am

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• $165 Multiple Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Portland, OR (PDX)	02/18/2025	07:05 am
  Portland, OR (PDX)	Chicago, IL (MDW)	02/24/2025	08:28 pm

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• $220 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Portland, OR (PDX)	03/27/2025	08:00 am
  Portland, OR (PDX)	Chicago, IL (ORD)	03/30/2025	02:33 pm

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• $81 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Portland, OR (PDX)	03/15/2025	06:40 am

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• $81 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Portland, OR (PDX)	03/15/2025	06:50 am

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• $127 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Portland, OR (PDX)	02/13/2025	10:45 pm

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• $146 Frontier Airlines 

  From	To	Departure	Time
  Chicago, IL (MDW)	Portland, OR (PDX)	02/13/2025	06:40 am

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• $197 Spirit Airlines 

  From	To	Departure	Time
  Chicago, IL (ORD)	Portland, OR (PDX)	03/15/2025	10:49 am

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