Route Price Intelligence
Cheap Flights From Portland to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$299
Deals From
$276
Usually Costs
$276 – $316
Lowest We've Seen
$115
Based on 8,658 price pointshigh confidence
Monthly Price Guide
Jan
$316
Feb
$316
Mar
$500
Apr
$279
May
$270
Jun
$295
Jul
$290
Aug
$275
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 $270. The most expensive month tends to be March at around $500. For the best deals, consider flying in May, August, April.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $11584 price checksWorst: $212