Cheapest return MDW–SJU flights, August

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

Return flights

18 Aug - 25 Aug Southwest Airlines
17 Aug - 21 Aug Southwest Airlines
20 Aug - 02 Sep Delta
21 Aug - 27 Aug Southwest Airlines
27 Aug - 31 Aug Southwest Airlines
28 Aug - 02 Sep Southwest Airlines
12 Aug - 19 Aug Southwest Airlines
11 Aug - 16 Aug Southwest Airlines
07 Aug - 14 Aug Southwest Airlines
08 Aug - 15 Aug Southwest Airlines
10 Aug - 17 Aug Frontier Airlines
15 Aug - 18 Aug Frontier Airlines

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

Powered by

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.

Book a cheap hotel in San Juan

Cheap car rent in San Juan

Feel free to contact us with any feedback or request another flight research.