Route Price Intelligence
Cheap Flights From San Diego to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$307
Deals From
$250
Usually Costs
$250 – $347
Lowest We've Seen
$95
Based on 8,486 price pointshigh confidence
Monthly Price Guide
Jan
$347
Feb
$347
Mar
$390
Apr
$230
May
$235
Jun
$290
Jul
$290
Aug
$270
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 April, when fares average around $230. The most expensive month tends to be March at around $390. For the best deals, consider flying in April, May, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9589 price checksWorst: $287