Route Price Intelligence
Cheap Flights From Portland to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$276
Deals From
$256
Usually Costs
$256 – $322
Lowest We've Seen
$156
Based on 8,387 price pointshigh confidence
Monthly Price Guide
Jan
$477
Feb
$262
Mar
$227
Apr
$217
May
$256
Jun
$288
Jul
$276
Aug
$266
Sep
$267
Oct
$413
Nov
$373
Dec
$569
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 $217. The most expensive month tends to be December at around $569. For the best deals, consider flying in April, March, May.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $15658 price checksWorst: $270