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 – $421
Lowest We've Seen
$156
Based on 3,755 price pointshigh confidence
Monthly Price Guide
Jan
$347
Feb
$414
Mar
$1,428
Apr
$546
May
$316
Jun
$326
Jul
$316
Aug
$316
Sep
$316
Oct
$336
Nov
$488
Dec
$583
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 $1,428. 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: $19173 price checksWorst: $316