Cheapest one-way flights from Chicago to San Juan in April from $58

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

AirHint found the following cheapest one-way flights from Chicago (MDW) to San Juan (SJU) in April 2025 (see full year).

One-Way flights

07 Apr Frontier Airlines
03 Apr Frontier Airlines
12 Apr Frontier Airlines
09 Apr Frontier Airlines
10 Apr Frontier Airlines
15 Apr Frontier Airlines
28 Apr Frontier Airlines
25 Apr Frontier Airlines
16 Apr Frontier Airlines
24 Apr Frontier Airlines

Also check the deals for return 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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