Cheapest return flights from Chicago to San Juan in July from $448

Best time to book flights for Chicago (MDW) to San Juan (SJU) flights at AirHint

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

Return flights

04 Jul - 10 Jul Southwest Airlines
15 Jul - 31 Jul Southwest Airlines
15 Jul - 22 Jul Southwest Airlines
10 Jul - 17 Jul Southwest Airlines
02 Jul - 06 Jul Southwest Airlines
10 Jul - 13 Jul Southwest Airlines
02 Jul - 02 Jul Southwest Airlines
22 Jul - 27 Jul Southwest Airlines
19 Jul - 25 Jul Southwest Airlines
15 Jul - 29 Jul Delta
26 Jul - 02 Aug Frontier Airlines
30 Jul - 04 Aug Frontier Airlines

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

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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