Cheapest one-way flights from Chicago (MDW) to San Juan (SJU), July

Select a price to book. see full year.

Dates, airline, and price
Dates Airline Price
27 Jul Southwest Airlines
28 Jul Southwest Airlines
25 Jul Southwest Airlines
20 Jul Southwest Airlines
21 Jul Southwest Airlines
26 Jul Southwest Airlines
31 Jul Allegiant Air
30 Jul Southwest Airlines
22 Jul Frontier Airlines
26 Jul Southwest Airlines
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deals for return flights from Chicago to San Juan in July.

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Updated Jul 19, 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.

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