Route Price Intelligence
Cheap Flights From Chicago to Portland
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$357
Great Deal
Under $357
Typical Range
$357 – $398
Lowest We've Seen
$115
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$357
Feb
$357
Mar
$357
Apr
$357
May
$357
Jun
$357
Jul
—
Aug
—
Sep
$404
Oct
$349
Nov
$357
Dec
$360
Cheapest Average Expensive
Best Time to Fly from Chicago to Portland
The cheapest time to fly from Chicago to Portland is typically October, when fares average around $349. The most expensive month tends to be September at around $404. For the best deals, consider flying in October, November, January.
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: September27,658 fares analyzedTypical low: $267