Route Price Intelligence
Cheap Flights From San Diego to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$306
Deals From
$250
Usually Costs
$250 – $347
Lowest We've Seen
$95
Based on 8,398 price pointshigh confidence
Monthly Price Guide
Jan
$347
Feb
$347
Mar
$412
Apr
$250
May
$230
Jun
$270
Jul
$270
Aug
$250
Sep
$347
Oct
$347
Nov
$347
Dec
$347
Cheapest Average Expensive
Best Time to Fly from San Diego to Chicago
The cheapest time to fly from San Diego to Chicago is typically May, when fares average around $230. The most expensive month tends to be March at around $412. For the best deals, consider flying in May, April, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9590 price checksWorst: $287