Cheap flights from Chicago to Portland
from 246 US$
Compare hundreds of airlines Chicago–Portland
The cheapest month is usually 2026-10 · 246 US$
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About this route
Compare flights from Chicago to Portland, a about 1,425 km route (around 2h 17m nonstop). We gather live prices from hundreds of airlines and agencies so you can find the cheapest and book on the official site, with no hidden fees. Direct flights are available. Airlines such as United Airlines operate this route.
When to buy and when to fly
Prices by date
Fares found by date — cheapest days in green.
How to get the best price
Airlines on this route
FAQ
What's the cheapest month to fly Chicago to Portland?
It's usually 2026-10, from 246 USD. Use the price calendar to compare other dates.
How long is the flight from Chicago to Portland?
A nonstop flight takes about 2h 17m and covers around 1,425 km. Connecting itineraries take longer.
Are there direct flights from Chicago to Portland?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from Chicago to Portland?
United Airlines operate this route, among others. Compare them all in the results.
When should I book Chicago–Portland flights?
As a rule of thumb, booking 3–8 weeks ahead and avoiding weekends and holidays tends to give the best prices. Use the calendar to spot the cheapest dates.
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Chicago → Portland · Live fares from 100+ sites — free, with no hidden fees.