Cheapest return flights from Chicago to San Juan in July from $346

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

Return flights

12 Jul - 16 Jul Southwest Airlines
21 Jul - 28 Jul Southwest Airlines
29 Jul - 03 Aug Southwest Airlines
21 Jul - 05 Aug Southwest Airlines
17 Jul - 23 Jul Southwest Airlines
23 Jul - 06 Aug Southwest Airlines
12 Jul - 17 Jul Southwest Airlines
16 Jul - 20 Jul Southwest Airlines
19 Jul - 22 Jul Southwest Airlines
05 Jul - 10 Jul Southwest Airlines
17 Jul - 21 Jul Southwest Airlines
02 Jul - 06 Jul Southwest Airlines
22 Jul - 26 Jul Frontier Airlines
31 Jul - 02 Aug Southwest Airlines
17 Jul - 02 Aug Frontier Airlines

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

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.