Route Price Intelligence
Cheap Flights From Chicago to Portland
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$378
Great Deal
Under $341
Typical Range
$341 – $384
Lowest We've Seen
$115
Based on 327 price pointshigh confidence
Monthly Price Guide
Jan
$378
Feb
$378
Mar
$384
Apr
$384
May
$384
Jun
$384
Jul
$406
Aug
$309
Sep
$286
Oct
$297
Nov
$360
Dec
$388
Cheapest Average Expensive
Best Time to Fly from Chicago to Portland
The cheapest time to fly from Chicago to Portland is typically September, when fares average around $286. The most expensive month tends to be July at around $406. For the best deals, consider flying in September, October, August.
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: August43,987 fares analyzedTypical low: $256