Route Price Intelligence
Cheap Flights From San Diego to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$357
Deals From
$347
Usually Costs
$347 – $367
Lowest We've Seen
$136
Based on 542 price pointshigh confidence
Monthly Price Guide
Jan
$367
Feb
—
Mar
—
Apr
$574
May
$285
Jun
$333
Jul
$357
Aug
$347
Sep
$347
Oct
$347
Nov
$457
Dec
$457
Cheapest Average Expensive
Best Time to Fly from San Diego to Chicago Midway
The cheapest time to fly from San Diego to Chicago Midway is typically May, when fares average around $285. The most expensive month tends to be April at around $574. For the best deals, consider flying in May, June, October.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $13668 price checksWorst: $267