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

Select a price to book. see full year.

Dates, airline, and price
Dates Airline Price
10 Jul 16 Jul Southwest Airlines
20 Jul 23 Jul Southwest Airlines
28 Jul 04 Aug Southwest Airlines
28 Jul 06 Aug Southwest Airlines
13 Jul 15 Jul Southwest Airlines
25 Jul 01 Aug Southwest Airlines
25 Jul 03 Aug Southwest Airlines
14 Jul 17 Jul Southwest Airlines
16 Jul 23 Jul Southwest Airlines
12 Jul 16 Jul Southwest Airlines
27 Jul 30 Jul Southwest Airlines
11 Jul 15 Jul Southwest Airlines
07 Jul 10 Jul Southwest Airlines
07 Jul 11 Jul Southwest Airlines
30 Jul 03 Aug Southwest Airlines
28 Jul 05 Aug Southwest Airlines
30 Jul 06 Aug Southwest Airlines
31 Jul 07 Aug Frontier Airlines
24 Jul 01 Aug Southwest Airlines
31 Jul 04 Aug Southwest Airlines
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deals for one-way flights from Chicago to San Juan in July.

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Updated Jul 6, 2026.

About these fares

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