Cheap flights from Chicago (ORD) to San Jose (SJO)
Cheapest round-trip I’ve found: US$379 on COPA, 1 stop(s), departing 2026-10-22. That’s US$299 below the typical price for this route.
Deal score: Not enough data yet
1stops
11h 58mflight time
Oct 2026cheapest departure window
US$678typical price
Best months to fly Chicago to San Jose
| Month | Cheapest seen |
|---|---|
| October | US$379 |
| August | US$614 |
How to book this fare
I don’t sell tickets — I track prices and point you to where to look. To book this fare:
- Search Chicago to San Jose on Google Flights for the dates shown above (Oct 2026) — the fare I found is usually still available there.
- Compare the same dates on metasearch sites like Skyscanner or KAYAK to confirm you’re seeing the lowest price.
- Book directly with the airline when you can — it’s often the same price and makes changes or cancellations much easier.
Fares change constantly. If the price has moved, check back — I re-check this route daily.
Other cheap flights from Chicago
- Chicago to Bali — US$923
- Chicago to Amsterdam — US$672
- Chicago to Honolulu — US$546
- Chicago to Seoul — US$1,125
- Chicago to Bangkok — US$830
- Chicago to Madrid — US$548
- Chicago to Delhi — US$762
- Chicago to Athens — US$600
Prices last checked: 2026-07-25, 6:07:18 a.m.. Prices are indicative and change quickly — confirm on the airline site before booking. See how I find these deals.