Cheapest return MDW–SJU flights, July

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

Return flights

04 Jul - 09 Jul Southwest Airlines
14 Jul - 18 Jul Frontier Airlines
12 Jul - 18 Jul Frontier Airlines
07 Jul - 09 Jul Southwest Airlines
18 Jul - 25 Jul Frontier Airlines
01 Jul - 06 Jul Frontier Airlines
15 Jul - 20 Jul Frontier Airlines
25 Jul - 01 Aug Frontier Airlines
14 Jul - 22 Jul Southwest Airlines
04 Jul - 07 Jul Southwest Airlines
04 Jul - 11 Jul Southwest Airlines
24 Jul - 01 Aug Southwest Airlines
25 Jul - 02 Aug Delta

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.