Cheapest return MDW–SJU flights, June

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

Return flights

03 Jun - 06 Jun Frontier Airlines
04 Jun - 07 Jun Frontier Airlines
02 Jun - 06 Jun Frontier Airlines
04 Jun - 08 Jun Frontier Airlines
03 Jun - 13 Jun Frontier Airlines
05 Jun - 12 Jun Frontier Airlines
23 Jun - 29 Jun Frontier Airlines
09 Jun - 16 Jun Frontier Airlines
16 Jun - 25 Jun Frontier Airlines
18 Jun - 23 Jun Frontier Airlines
29 Jun - 04 Jul Frontier Airlines
29 Jun - 03 Jul Southwest Airlines
28 Jun - 04 Jul Frontier Airlines
30 Jun - 09 Jul Southwest Airlines
25 Jun - 02 Jul Southwest Airlines
27 Jun - 08 Jul Southwest Airlines
27 Jun - 04 Jul Southwest Airlines
30 Jun - 07 Jul Southwest Airlines

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

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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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