Cheap flights from PDX to Chicago
Recently found return fares from $186, with October the cheapest month we know of. Compare dates, then book with the partner you choose.
Cheapest months to fly
Lowest recently found return fare in each month. Tap a month to see that month's calendar.
PDX → Chicago
November 2026
Lowest fares for the best day
- American AirlinesWed 25 Nov – Sun 29 Nov · 1 stop · 6h 28m $247
- Frontier AirlinesThu 12 Nov – Sun 15 Nov · 1 stop · 4h 59m $315
- United AirlinesFri 13 Nov – Sun 15 Nov · Direct · 3h 49m $352
- Frontier AirlinesSun 8 Nov – Tue 10 Nov · 1 stop · 5h 58m $356
- Alaska AirlinesSat 7 Nov – Mon 9 Nov · Direct · 4h 08m $370
Airports in Chicago
- ORDO'Hare
- MDWMidway
Watch this route
FAQ
Questions about this route
Search the help center or send us a message. We reply by email.
Help center Contact us01What is the cheapest month to fly from PDX to Chicago?
Based on recently found fares, October 2026 has the lowest price we know of, from $186. Prices change often, so check the calendar for current fares.
02Which airports serve Chicago?
Chicago is served by O'Hare (ORD), Midway (MDW). Searching the city code compares all of them at once.
03Are the prices on this page final?
No. They are recently found fares. When you open a deal, the partner shows the live price, including taxes and fees, before you pay.
04How can I get an alert when flights to Chicago get cheaper?
Use the price alert on this page. Choose your dates or a whole month and we will email you when the fare drops.