AirHint found the following cheapest return flights from Chicago (ORD) to San Jose (SJO) in May 2026 (see full year).
Return flights
| 22 May - 10 Jun | Viva | ||
| 06 May - 16 May | Spirit Airlines | ||
| 06 May - 21 May | Spirit Airlines | ||
| 22 May - 31 May | Viva | ||
| 23 May - 10 Jun | Spirit Airlines | ||
| 23 May - 31 May | Spirit Airlines |
Also check the deals for one-way flights from Chicago to San Jose in May.
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