Route Price Intelligence
Cheap Flights From San Diego to Chicago
Live pricing benchmarks, monthly patterns, and historical lows for this route.
Typical Price
$305
Deals From
$250
Usually Costs
$250 – $347
Lowest We've Seen
$95
Based on 3,071 price pointshigh confidence
Monthly Price Guide
Jan
$347
Feb
$347
Mar
$347
Apr
$320
May
$230
Jun
$266
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 $230. The most expensive month tends to be September at around $347. For the best deals, consider flying in May, June, August.
Cheapest Fare Found (Last 90 Days)
The lowest round-trip price available on each day we checked
Best: $9570 price checksWorst: $287