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Flights from Portland to Illinois

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Flight deals from Portland to Illinois

Looking for cheap flights from Portland to Illinois, or a last-minute trip? Find the lowest prices on one-way and round-trip flights right here.
Chicago.$167 per passenger.Departing Sat, Jun 7, returning Sat, Jun 14.Round-trip flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departing from Portland on Sat, Jun 7, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departing from Chicago O'Hare International on Sat, Jun 14, arriving in Portland.Price includes taxes and charges.From $167, select.
Chicago.$177 per passenger.Departing Sat, May 24, returning Fri, May 30.Round-trip flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departing from Portland on Sat, May 24, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departing from Chicago Midway on Fri, May 30, arriving in Portland.Price includes taxes and charges.From $177, select.
Peoria.$316 per passenger.Departing Wed, May 14, returning Fri, May 23.Round-trip flight with United.Outbound indirect flight with United, departing from Portland on Wed, May 14, arriving in Greater Peoria.Inbound indirect flight with United, departing from Greater Peoria on Fri, May 23, arriving in Portland.Price includes taxes and charges.From $316, select.
Decatur.$419 per passenger.Departing Mon, Apr 28, returning Fri, May 9.Round-trip flight with United.Outbound indirect flight with United, departing from Portland on Mon, Apr 28, arriving in Decatur.Inbound indirect flight with United, departing from Decatur on Fri, May 9, arriving in Portland.Price includes taxes and charges.From $419, select.
Moline.$439 per passenger.Departing Wed, Apr 23, returning Tue, Apr 29.Round-trip flight with United.Outbound indirect flight with United, departing from Portland on Wed, Apr 23, arriving in Moline.Inbound indirect flight with United, departing from Moline on Tue, Apr 29, arriving in Portland.Price includes taxes and charges.From $439, select.

Flying from Portland to Illinois

Arm yourself with these facts on the fly.
Cheapest flight found$167, Chicago
Cheapest month to flyJune
Average flight time4 hrs, 1 min
Cheapest airport to fly fromPortland
Most popular airlineUnited

Frequently asked questions

We looked at all of the upcoming round-trip flights from Portland to Illinois we could find over the next 12 months. It looks like $167 is the best price. This is good, compared to the average Illinois ticket price of $282.
The cheapest month to fly from Portland to Moline Airport is usually April. The cheapest month to fly from Portland to Decatur Airport is usually April. The cheapest month to fly from Portland to Chicago Midway Airport is usually May. And the cheapest month to fly from Portland to Chicago O'Hare International Airport is usually June.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Portland to Illinois on Saturday, June 7, 2025.
Portland Airport offers direct flights to Illinois.
If you're flying from Portland, the cheapest city in Illinois to fly into is Chicago. The cheapest airport serving Chicago at the moment is Chicago O'Hare International.
The average flight time between Portland and Illinois is 4 hours.