Cheapest return flights from Chicago to San Juan in July from $232

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in July 2025 (see full year).

Return flights

14 Jul - 19 Jul Frontier Airlines
17 Jul - 19 Jul Frontier Airlines
13 Jul - 16 Jul Frontier Airlines
13 Jul - 19 Jul Frontier Airlines
14 Jul - 18 Jul Frontier Airlines
04 Jul - 09 Jul Frontier Airlines
21 Jul - 28 Jul Frontier Airlines
24 Jul - 31 Jul Frontier Airlines
04 Jul - 11 Jul Frontier Airlines
26 Jul - 02 Aug Frontier Airlines
24 Jul - 02 Aug Frontier Airlines
17 Jul - 21 Jul Frontier Airlines
27 Jul - 09 Aug Frontier Airlines
26 Jul - 03 Aug Frontier Airlines
31 Jul - 03 Aug Frontier Airlines
30 Jul - 05 Aug Southwest 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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