Route Price Intelligence
Cheap Flights From Portland to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$336
Deals From
$316
Usually Costs
$316 – $442
Lowest We've Seen
$156
Based on 329 price pointshigh confidence
Monthly Price Guide
Jan
$347
Feb
$416
Mar
$532
Apr
$576
May
$336
Jun
$327
Jul
$316
Aug
$316
Sep
$316
Oct
$336
Nov
$499
Dec
$589
Cheapest Average Expensive
Best Time to Fly from Portland to Chicago Midway
The cheapest time to fly from Portland to Chicago Midway is typically July, when fares average around $316. The most expensive month tends to be December at around $589. For the best deals, consider flying in July, August, September.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $19168 price checksWorst: $316