Route Price Intelligence
Cheap Flights From San Diego to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$285
Deals From
$232
Usually Costs
$232 – $287
Lowest We've Seen
$95
Based on 8,396 price pointshigh confidence
Monthly Price Guide
Jan
$306
Feb
$177
Mar
$187
Apr
$167
May
$221
Jun
$285
Jul
$285
Aug
$285
Sep
$285
Oct
$285
Nov
$285
Dec
$285
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 $167. The most expensive month tends to be January at around $306. For the best deals, consider flying in April, February, March.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9563 price checksWorst: $287