Cheapest return flights from Chicago (MDW) to San Juan (SJU), August

Select a price to book. see full year.

Dates, airline, and price
Dates Airline Price
31 Aug 02 Sep Southwest Airlines
28 Aug 01 Sep Southwest Airlines
28 Aug 03 Sep Southwest Airlines
28 Aug 02 Sep Southwest Airlines
28 Aug 29 Aug Southwest Airlines
28 Aug 31 Aug Southwest Airlines
28 Aug 04 Sep Southwest Airlines
29 Aug 02 Sep Southwest Airlines
30 Aug 02 Sep Southwest Airlines
30 Aug 03 Sep Southwest Airlines
30 Aug 05 Sep Southwest Airlines
30 Aug 01 Sep Southwest Airlines
28 Aug 28 Aug Southwest Airlines
26 Aug 30 Aug Frontier Airlines
30 Aug 30 Aug Frontier Airlines
27 Aug 30 Aug Frontier Airlines
29 Aug 30 Aug Frontier Airlines
28 Aug 30 Aug Southwest Airlines
26 Aug 28 Aug Southwest Airlines
26 Aug 29 Aug Southwest Airlines
Powered by

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

Book a cheap hotel in San Juan

Cheap car rent in Luis Munoz Marin Intl

Updated Aug 25, 2026.

About these fares

These results come from our latest search across airlines for your currency. Prices change quickly and are not locked until you complete booking—always confirm the total and fare rules on the partner site.

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