Route Price Intelligence
Cheap Flights From Portland to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$374
Great Deal
Under $260
Typical Range
$260 – $389
Lowest We've Seen
$156
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$374
Feb
$374
Mar
$394
Apr
$394
May
—
Jun
—
Jul
$432
Aug
$261
Sep
$238
Oct
$237
Nov
$308
Dec
$384
Cheapest Average Expensive
Best Time to Fly from Portland to Chicago Midway
The cheapest time to fly from Portland to Chicago Midway is typically October, when fares average around $237. The most expensive month tends to be July at around $432. For the best deals, consider flying in October, September, 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: August22,450 fares analyzedTypical low: $286