AirHint found the following cheapest return flights from Chicago (MDW) to San Jose (SJO) in October 2025 (see full year).
Return flights
| 21 Oct - 26 Oct | Frontier Airlines | ||
| 22 Oct - 27 Oct | Southwest Airlines | ||
| 21 Oct - 28 Oct | Delta | ||
| 20 Oct - 27 Oct | Southwest Airlines | ||
| 31 Oct - 08 Nov | Southwest Airlines |
Also check the deals for one-way flights from Chicago to San Jose in October.
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The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.
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