Open interactive map →Cheap flights from Chicago to Portland
Fares on the Chicago to Portland route are tracked month by month. The lowest observed price is €160. The cheapest tracked fare is non-stop. The calendar below lists the months SkyHopp has fares for - not enough months yet to name a cheapest month.
This is a tracked route from Chicago to Portland in United States. The lowest observed fare is €160. If your dates are flexible, compare the months that already have fares in the calendar.
One-way fares
From €160
Cheapest tracked fare (non-stop)
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Cheapest month to fly
- November 2026€160DirectCheapest
SkyHopp has tracked fares for this route in November at around €160. That is the only month with data so far, so it is too early to name a cheapest month.
Cheapest fare last seen 25 October 2026.
Entry requirements for United States
EU passportESTA required (visa-waiver)
US passportN/A (domestic)
Requirements vary by nationality and change without notice. Check requirements for your nationality →
Alternative routes
Other ways to reach Portland
Frequently asked questions
How much does a flight from Chicago to Portland cost?
The cheapest tracked fare from Chicago to Portland is €160. The month-by-month price calendar on this page lists the months SkyHopp has fares for. Fares are refreshed as our flight partners publish new availability.
Are there direct flights from Chicago to Portland?
Yes - non-stop fares appear in SkyHopp's tracked data from Chicago to Portland. The cheapest tracked fare, from €160, is itself non-stop. Click through to the booking site to check schedules for your dates.
When is the cheapest time to fly from Chicago to Portland?
SkyHopp does not yet have enough months of fares on this route to name a cheapest month. The calendar above lists the months that already have data. Set a price alert on this page to watch the fare.