Cheapest return flights from Chicago to San Jose in April from $395

Best time to book flights for Chicago (MDW) to San Jose (SJO) flights at AirHint

AirHint found the following cheapest return flights from Chicago (MDW) to San Jose (SJO) in April 2025 (see full year).

Return flights

25 Apr - 28 Apr Frontier Airlines
11 Apr - 30 Apr Frontier Airlines
21 Apr - 26 Apr Frontier Airlines
08 Apr - 15 Apr Frontier Airlines
11 Apr - 13 Apr Frontier Airlines
09 Apr - 13 Apr Frontier Airlines
18 Apr - 20 Apr Frontier Airlines
30 Apr - 10 May Southwest Airlines
03 Apr - 07 Apr Frontier Airlines
29 Apr - 05 May Southwest Airlines
07 Apr - 14 Apr Southwest Airlines
17 Apr - 20 Apr Frontier Airlines

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

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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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