Cheap flights from Portland to Chicago
from 168 US$
From 299 USD — compare hundreds of airlines
The cheapest month is usually 2026-08 · 168 US$
See prices for my dates →Live fares from 100+ sites — free, with no hidden fees.
About this route
Compare flights from Portland to Chicago, a about 2,816 km route (around 4h 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 Alaska Airlines, United Airlines, Southwest 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 Portland to Chicago?
It's usually 2026-08, from 168 USD. Use the price calendar to compare other dates.
How long is the flight from Portland to Chicago?
A nonstop flight takes about 4h and covers around 2,816 km. Connecting itineraries take longer.
Are there direct flights from Portland to Chicago?
Yes, this route has nonstop flights. Filter by "nonstop" to see them.
Which airlines fly from Portland to Chicago?
Alaska Airlines, United Airlines, Southwest Airlines operate this route, among others. Compare them all in the results.
When should I book Portland–Chicago 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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Portland → Chicago · Live fares from 100+ sites — free, with no hidden fees.