August is the cheapest month to fly this route, with average fares around $233 round trip.
Average round-trip fares by departure month, based on current availability.
| Month | Avg Price | Lowest | Relative Cost | |
|---|---|---|---|---|
| May 2026 | $293 | $230 | Peak | |
| June 2026 | $250 | $210 | ||
| July 2026 | $254 | $230 | ||
| August 2026 | $233 | $230 | Best |
Departing on Tuesday offers the lowest average fares at $244. Friday departures are the most expensive at $268, a difference of $24.
The best time to fly is August. Set up an alert and we'll notify you when prices drop.
Get Started Free →The cheapest month to fly from San Diego to Chicago is August, with average round-trip fares around $233. The lowest fare found in August is $230.
Tuesday departures are the cheapest, averaging $244 round trip. The most expensive day is Friday at $268.
Based on current pricing trends, booking for August travel offers the best value. Avoid May if possible, as fares average $293 compared to $233 in the cheapest month. July is a solid middle-ground option at $254.
Flying in August instead of May can save you approximately $60 per round trip. The cheapest month averages $233 while the most expensive averages $293.
Airlines, flight times, price calendar, and more for San Diego to Chicago
View SAN → ORD Details