Cheapest return MDW–SJO flights, July

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

Return flights

31 Jul - 12 Aug Southwest Airlines
04 Jul - 11 Jul Frontier Airlines
28 Jul - 28 Jul Delta
25 Jul - 01 Aug Southwest Airlines
29 Jul - 05 Aug Southwest Airlines
31 Jul - 13 Aug Southwest Airlines
18 Jul - 25 Jul Frontier Airlines
31 Jul - 11 Aug Southwest Airlines
27 Jul - 28 Jul Southwest Airlines
09 Jul - 16 Jul Delta
11 Jul - 18 Jul Frontier Airlines
02 Jul - 06 Jul Southwest Airlines
16 Jul - 28 Jul Southwest Airlines
16 Jul - 29 Jul Southwest Airlines
15 Jul - 28 Jul Southwest Airlines
26 Jul - 02 Aug Southwest Airlines
17 Jul - 01 Aug Southwest Airlines

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

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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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