Cheapest return flights from Chicago to San Juan in April from $267

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

08 Apr - 18 Apr Frontier Airlines
12 Apr - 14 Apr Frontier Airlines
14 Apr - 18 Apr Frontier Airlines
07 Apr - 14 Apr Frontier Airlines
11 Apr - 14 Apr Frontier Airlines
14 Apr - 21 Apr Frontier Airlines
09 Apr - 15 Apr Frontier Airlines
11 Apr - 15 Apr Frontier Airlines
14 Apr - 24 Apr Frontier Airlines
08 Apr - 15 Apr Frontier Airlines
24 Apr - 01 May Frontier Airlines
25 Apr - 02 May Frontier Airlines
24 Apr - 03 May Frontier Airlines
29 Apr - 06 May Delta
29 Apr - 08 May Delta
30 Apr - 04 May Southwest 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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