Cheapest return flights from Chicago to San Juan in August from 241€

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

Return flights

31 Aug - 04 Sep Frontier Airlines
14 Aug - 21 Aug Frontier Airlines
08 Aug - 14 Aug Frontier Airlines
17 Aug - 21 Aug Frontier Airlines
25 Aug - 30 Aug Frontier Airlines
17 Aug - 23 Aug Frontier Airlines
18 Aug - 21 Aug Frontier Airlines
16 Aug - 22 Aug Frontier Airlines
18 Aug - 25 Aug Frontier Airlines
29 Aug - 08 Sep Frontier Airlines
17 Aug - 24 Aug Frontier Airlines
28 Aug - 04 Sep Frontier Airlines
30 Aug - 03 Sep Frontier Airlines
31 Aug - 03 Sep Frontier Airlines
15 Aug - 20 Aug Frontier Airlines
29 Aug - 01 Sep Frontier Airlines
27 Aug - 01 Sep Southwest Airlines

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

Skyscanner

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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