Cheapest return flights from Chicago to San Juan in June from 426€

Best time to book flights for Chicago (MDW) to San Juan (SJU) flights at AirHint

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in June 2025 (see full year).

Return flights

01 Jun - 10 Jun Southwest Airlines
20 Jun - 24 Jun Southwest Airlines
05 Jun - 09 Jun Southwest Airlines
19 Jun - 24 Jun Southwest Airlines
06 Jun - 09 Jun Southwest Airlines
20 Jun - 23 Jun Southwest Airlines
29 Jun - 03 Jul Southwest Airlines
21 Jun - 28 Jun Southwest Airlines
05 Jun - 11 Jun Delta
13 Jun - 21 Jun Delta
05 Jun - 08 Jun Frontier Airlines

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

Skyscanner

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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