Cheapest return flights from Chicago to San Juan in July from 292€

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

Return flights

14 Jul - 13 Aug Southwest Airlines
29 Jul - 03 Aug Frontier Airlines
04 Jul - 06 Jul Frontier Airlines
16 Jul - 20 Jul Southwest Airlines
05 Jul - 12 Jul Frontier Airlines
10 Jul - 13 Jul Southwest Airlines
11 Jul - 12 Jul Frontier Airlines
30 Jul - 03 Aug Frontier Airlines
30 Jul - 04 Aug Frontier Airlines
29 Jul - 02 Aug Southwest Airlines
03 Jul - 05 Jul Southwest Airlines
09 Jul - 12 Jul Southwest Airlines
23 Jul - 26 Jul Southwest Airlines
10 Jul - 12 Jul Southwest Airlines
10 Jul - 10 Jul Southwest Airlines
25 Jul - 02 Aug Frontier Airlines

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

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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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