Route Price Intelligence
Cheap Flights From Portland to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$316
Great Deal
Under $291
Typical Range
$291 – $316
Lowest We've Seen
$115
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$291
Feb
$291
Mar
$316
Apr
$325
May
$280
Jun
$295
Jul
$309
Aug
$298
Sep
$316
Oct
$316
Nov
$316
Dec
$325
Cheapest Average Expensive
Best Time to Fly from Portland to Chicago
The cheapest time to fly from Portland to Chicago is typically May, when fares average around $280. The most expensive month tends to be April at around $325. For the best deals, consider flying in May, January, February.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: November5,889 fares analyzedTypical low: $316
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