AirHint found the following cheapest one-way flights from Chicago (ORD) to San Jose (SJO) in May 2026 (see full year).
One-Way flights
| 16 May | Air Canada | ||
| 12 May | Southwest Airlines | ||
| 14 May | Volaris | ||
| 10 May | Volaris | ||
| 11 May | Copa | ||
| 13 May | Copa | ||
| 16 May | United | direct |
Also check the deals for return flights from Chicago to San Jose in May.
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