Route Price Intelligence
Cheap Flights From San Diego to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$330
Great Deal
Under $280
Typical Range
$280 – $388
Lowest We've Seen
$95
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$267
Feb
$281
Mar
$351
Apr
$351
May
$361
Jun
$417
Jul
$417
Aug
—
Sep
—
Oct
$377
Nov
$272
Dec
$282
Cheapest Average Expensive
Best Time to Fly from San Diego to Chicago
The cheapest time to fly from San Diego to Chicago is typically January, when fares average around $267. The most expensive month tends to be July at around $417. For the best deals, consider flying in January, November, February.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route
Cheapest month: October9,646 fares analyzedTypical low: $287