Cheapest return MDW–SJU flights, July

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

Return flights

14 Jul - 18 Jul Frontier Airlines
04 Jul - 09 Jul Southwest Airlines
09 Jul - 13 Jul Frontier Airlines
21 Jul - 27 Jul Frontier Airlines
07 Jul - 14 Jul Frontier Airlines
04 Jul - 06 Jul Southwest Airlines
07 Jul - 13 Jul Southwest Airlines
29 Jul - 03 Aug Southwest Airlines
11 Jul - 16 Jul Southwest Airlines
07 Jul - 09 Jul Southwest Airlines
25 Jul - 01 Aug Southwest Airlines
01 Jul - 06 Jul Frontier Airlines
31 Jul - 07 Aug Southwest Airlines
24 Jul - 01 Aug Southwest Airlines
31 Jul - 03 Aug Southwest Airlines
25 Jul - 02 Aug Frontier Airlines

Also check the deals for one-way flights from Chicago to San Juan 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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