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
$290
Usually Costs
$290 – $316
Lowest We've Seen
$115
Based on 5,237 price pointshigh confidence
Monthly Price Guide
Jan
$316
Feb
$316
Mar
$316
Apr
$391
May
$275
Jun
$290
Jul
$295
Aug
$290
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 $275. The most expensive month tends to be April at around $391. 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: $11579 price checksWorst: $212