Route Price Intelligence
Cheap Flights From San Diego to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$284
Great Deal
Under $227
Typical Range
$227 – $377
Lowest We've Seen
$95
Based on 678 price pointshigh confidence
Monthly Price Guide
Jan
$250
Feb
$265
Mar
$328
Apr
$284
May
$340
Jun
$397
Jul
$377
Aug
—
Sep
—
Oct
$284
Nov
$272
Dec
$262
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 $250. The most expensive month tends to be June at around $397. For the best deals, consider flying in January, December, 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: November5,882 fares analyzedTypical low: $347
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