Route Price Intelligence
Cheap Flights From Portland to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$316
Deals From
$295
Usually Costs
$295 – $316
Lowest We've Seen
$115
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$316
Feb
—
Mar
—
Apr
$469
May
$280
Jun
$295
Jul
$309
Aug
$298
Sep
$316
Oct
$316
Nov
$316
Dec
$327
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 $469. For the best deals, consider flying in May, June, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $11570 price checksWorst: $212