San Diego International (SAN) to O'Hare International (ORD).
| Departure | Return | Price |
|---|---|---|
| 06/03/2026 | 06/09/2026 | $210 |
| 05/28/2026 | 06/03/2026 | $230 |
| 05/31/2026 | 06/09/2026 | $230 |
| 06/01/2026 | 06/09/2026 | $230 |
| 06/02/2026 | 06/09/2026 | $230 |
| 06/03/2026 | 06/10/2026 | $230 |
| 06/03/2026 | 06/11/2026 | $230 |
| 06/03/2026 | 06/12/2026 | $230 |
| 06/09/2026 | 06/17/2026 | $230 |
| 06/10/2026 | 06/17/2026 | $230 |
Based on current fares, August is the cheapest month to fly from San Diego to Chicago, with average fares around $233 round trip (as low as $230).
May tends to be more expensive, averaging $293.
See the full month-by-month and day-of-week price analysis
Best Time to Fly SAN → ORDDeparture date prices (economy, round trip). Green = cheap, red = expensive.
The cheapest month to fly from San Diego to Chicago is August, with average round-trip fares around $233. Fares in August start as low as $230. The most expensive month is May, averaging $293.
A nonstop flight from San Diego to Chicago takes approximately 4h.
The cheapest flight from San Diego to Chicago currently starts at $210 round trip in economy class.
The average round-trip flight price from San Diego to Chicago is $273 in economy class.
The distance is 1723 miles (2772 km). with a nonstop flight time of about 4h. The lowest fare currently available is $210 departing in June. The average round-trip fare is $273.
Set up a guest alert and we'll keep checking prices for you. No account needed.
Get Started Free →