Route Price Intelligence
Cheap Flights From San Diego to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$347
Great Deal
Under $270
Typical Range
$270 – $347
Lowest We've Seen
$95
Based on 271 price pointshigh confidence
Monthly Price Guide
Jan
$347
Feb
—
Mar
—
Apr
$361
May
$250
Jun
$270
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 May, when fares average around $250. The most expensive month tends to be April at around $361. For the best deals, consider flying in May, June, August.
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: July21,882 fares analyzedTypical low: $285