Route Price Intelligence
Cheap Flights From Portland to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$327
Deals From
$316
Usually Costs
$316 – $366
Lowest We've Seen
$156
Based on 8,558 price pointshigh confidence
Monthly Price Guide
Jan
$336
Feb
$401
Mar
$548
Apr
$309
May
$309
Jun
$317
Jul
$316
Aug
$316
Sep
$316
Oct
$342
Nov
$402
Dec
$532
Cheapest Average Expensive
Best Time to Fly from Portland to Chicago Midway
The cheapest time to fly from Portland to Chicago Midway is typically April, when fares average around $309. The most expensive month tends to be March at around $548. For the best deals, consider flying in April, May, July.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $15686 price checksWorst: $316