Cheapest return flights from Chicago to San Juan in April from $404

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 April 2025 (see full year).

Return flights

12 Apr - 14 Apr Southwest Airlines
24 Apr - 29 Apr Southwest Airlines
15 Apr - 23 Apr Frontier Airlines
01 Apr - 06 Apr Frontier Airlines
24 Apr - 01 May Frontier Airlines
26 Apr - 03 May Frontier Airlines
25 Apr - 28 Apr Frontier Airlines
03 Apr - 06 Apr Southwest Airlines
10 Apr - 14 Apr Frontier Airlines
05 Apr - 10 Apr Frontier Airlines
24 Apr - 27 Apr Frontier Airlines
17 Apr - 21 Apr Frontier Airlines

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

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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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