Route Price Intelligence
Cheap Flights From San Diego to Chicago Midway
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$347
Deals From
$334
Usually Costs
$334 – $369
Lowest We've Seen
$136
Based on 4,236 price pointshigh confidence
Monthly Price Guide
Jan
$387
Feb
$393
Mar
$1,003
Apr
$450
May
$267
Jun
$332
Jul
$357
Aug
$347
Sep
$347
Oct
$347
Nov
$387
Dec
$393
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 $267. The most expensive month tends to be March at around $1,003. 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: $13673 price checksWorst: $267