Route Price Intelligence
Cheap Flights From Portland to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$276
Deals From
$256
Usually Costs
$256 – $315
Lowest We've Seen
$115
Based on 8,428 price pointshigh confidence
Monthly Price Guide
Jan
$458
Feb
$227
Mar
$208
Apr
$207
May
$232
Jun
$256
Jul
$256
Aug
$256
Sep
$256
Oct
$256
Nov
$256
Dec
$266
Cheapest Average Expensive
Best Time to Fly from Portland to Chicago
The cheapest time to fly from Portland to Chicago is typically April, when fares average around $207. The most expensive month tends to be January at around $458. For the best deals, consider flying in April, March, February.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $11571 price checksWorst: $221