Cheapest return flights from Chicago to San Jose in February from 267€

AirHint found the following cheapest return flights from Chicago (MDW) to San Jose (SJO) in February 2026 (see full year).

Return flights

23 Feb - 28 Feb Frontier Airlines
20 Feb - 25 Feb Frontier Airlines
04 Feb - 12 Feb Southwest Airlines
04 Feb - 10 Feb Southwest Airlines
05 Feb - 26 Feb Southwest Airlines
17 Feb - 25 Feb Delta
26 Feb - 05 Mar Frontier Airlines
04 Feb - 19 Feb Southwest Airlines
01 Feb - 07 Feb Delta
24 Feb - 03 Mar Delta
04 Feb - 25 Feb Southwest Airlines
19 Feb - 23 Feb Delta
28 Feb - 07 Mar Frontier Airlines
26 Feb - 06 Mar Delta

Also check the deals for one-way flights from Chicago to San Jose in February.

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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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