Portland to Chicago flights
Round trip · Economy · Prices per person in USD
Prices updated
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when Portland → Chicago drops below your price.Cheapest dates in the next 4 months
Round trip, per person-
Oct 22 – 25 3 nights · leave Thu$244$244 Book
Southwest Airlines 1 stop · 5h 45m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
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Airport transfer to Chicago
Fixed prices from ORD on KiwitaxiTo see transfer prices here, turn on partner content in .
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Plan the rest of your trip
Chicago · Oct 22 – 25Travel insurance · EKTA Airport transfer · Kiwitaxi
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Portland to Chicago: questions
How much is a flight from Portland to Chicago?
The cheapest round trip we have found right now is $244, leaving October 22 and returning October 25. Prices are per person, economy, in USD.
About this route
We track round-trip economy fares from Portland (United States) to Chicago (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $244, departing October 22 and returning October 25. The cheapest month to fly in our data is October, from $244. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.