Cheapest return flights from Chicago (ORD) to San Jose (SJO), October

20 dates in October, from $ 381. Book in one tap, or check whether to buy now or wait.

One-wayReturn
Dates, airline, and price
Dates Airline Price
16 Oct 24 Oct Frontier Airlines
27 Oct 5 Nov Avianca
31 Oct 14 Nov Avianca
28 Oct 3 Nov Avianca
31 Oct 2 Nov Avianca
31 Oct 7 Nov Avianca
27 Oct 2 Nov Avianca
28 Oct 31 Oct Avianca
30 Oct 1 Nov Copa
23 Oct 26 Oct Copa
31 Oct 7 Nov United
Direct Flight
31 Oct 10 Nov American Airlines
28 Oct 5 Nov Avianca
24 Oct 26 Oct United
21 Oct 25 Oct Copa
19 Oct 26 Oct American Airlines
17 Oct 19 Oct United
16 Oct 23 Oct American Airlines
16 Oct 20 Oct American Airlines
21 Oct 24 Oct American Airlines
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Deals for one-way flights from Chicago to San Jose in October.

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Updated Oct 15, 2026.

About these fares

These results come from our latest search across airlines for your currency. Prices change quickly and are not locked until you complete booking—always confirm the total and fare rules on the partner site.

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