Cheap flights from Chicago to Portland
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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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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
![Price overview for flights from Chicago to Portland Price overview for flights from Chicago to Portland](/images/new/cheap-flights/graph/cheap-flights-from-Chicago-to-Portland-graph.png?date=202502)
Recent Deals on Flights from Chicago to Portland:Roundtrip / Oneway
- $135
Frontier Airlines
cheapoair.com check priceFrom 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 - $135
Frontier Airlines
cheapoair.com check priceFrom 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 - $149
Multiple Airlines
cheapoair.com check priceFrom 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 - $165
Multiple Airlines
cheapoair.com check priceFrom 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 - $220
Spirit Airlines
cheapoair.com check priceFrom 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 - $81
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Portland, OR (PDX) 03/15/2025 06:40 am - $81
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Portland, OR (PDX) 03/15/2025 06:50 am - $127
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Portland, OR (PDX) 02/13/2025 10:45 pm - $146
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (MDW) Portland, OR (PDX) 02/13/2025 06:40 am - $197
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Portland, OR (PDX) 03/15/2025 10:49 am
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Know what to do when flying to Portland?
Portland Travel Guide Portland is a city full of life, located where the Columbia and Willamette rivers meet was a good starting point for its becoming the third-largest port on the West Coast. For decades people looking for something of a more sophisticated [...]Portland History Situated at the mouth of Fore River, Portland is a historic port at the Atlantic and the largest city in the state of Maine, US. Portland history can be seen as a story of destruction and renewal: across its almost four centuries of existence, [...]
Portland Sightseeing Portland is a beautiful city in the US. It is situated in the northwest and it is also known as America's best kept secret. Portland is also referred to as the greenest city in the United States. The city is full of entertainment spots and [...]
Portland Nightlife Portland is a place to have fun with your friends and families. It has to offer something to all.There are a lot of martini-type bars, comedy clubs, hangout places, nightclubs, bars, pubs, restaurants, discos and nightlife entertainment spots [...]