Cheapest return flights from Chicago to San Juan in June from 357€

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

Return flights

17 Jun - 24 Jun Southwest Airlines
09 Jun - 16 Jun Southwest Airlines
03 Jun - 10 Jun Southwest Airlines
23 Jun - 30 Jun Southwest Airlines
08 Jun - 14 Jun Southwest Airlines
10 Jun - 17 Jun Southwest Airlines
01 Jun - 08 Jun Southwest Airlines
11 Jun - 14 Jun Southwest Airlines
13 Jun - 20 Jun Southwest Airlines
26 Jun - 05 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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