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 – $391
Lowest We've Seen
$156
Based on 8,616 price pointshigh confidence
Monthly Price Guide
Jan
$336
Feb
$412
Mar
$572
Apr
$406
May
$316
Jun
$326
Jul
$316
Aug
$316
Sep
$316
Oct
$342
Nov
$421
Dec
$552
Cheapest Average Expensive
Best Time to Fly from Portland to Chicago Midway
The cheapest time to fly from Portland to Chicago Midway is typically May, when fares average around $316. The most expensive month tends to be March at around $572. For the best deals, consider flying in May, July, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $19189 price checksWorst: $316