Cheapest return flights from Chicago to San Juan in June from 322€

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

Return flights

15 Jun - 18 Jun Southwest Airlines
15 Jun - 23 Jun Southwest Airlines
08 Jun - 18 Jun Southwest Airlines
17 Jun - 24 Jun Southwest Airlines
01 Jun - 08 Jun Southwest Airlines
16 Jun - 23 Jun Southwest Airlines
04 Jun - 09 Jun Southwest Airlines
23 Jun - 30 Jun Southwest Airlines
03 Jun - 13 Jun Southwest Airlines
15 Jun - 22 Jun Southwest Airlines
27 Jun - 02 Jul WestJet

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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