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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

$191$222$254$285$316Feb 6Mar 14Apr 19
Best: $19173 price checksWorst: $316
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