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 | $283 | $230 | Peak | |
| June 2026 | $258 | $210 | ||
| July 2026 | $244 | $210 | ||
| August 2026 | $233 | $230 | Best |
Departing on Tuesday offers the lowest average fares at $233. Friday departures are the most expensive at $272, a difference of $39.
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 Francisco 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 $233 round trip. The most expensive day is Friday at $272.
Based on current pricing trends, booking for August travel offers the best value. Avoid May if possible, as fares average $283 compared to $233 in the cheapest month. June is a solid middle-ground option at $258.
Flying in August instead of May can save you approximately $50 per round trip. The cheapest month averages $233 while the most expensive averages $283.
Airlines, flight times, price calendar, and more for San Francisco to Chicago
View SFO → ORD Details