Cheapest return flights from Chicago to San Juan in May from $272

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 May 2025 (see full year).

Return flights

12 May - 15 May Frontier Airlines
19 May - 29 May Frontier Airlines
05 May - 08 May Frontier Airlines
09 May - 11 May Frontier Airlines
15 May - 17 May Frontier Airlines
08 May - 11 May Frontier Airlines
09 May - 12 May Frontier Airlines
04 May - 09 May Frontier Airlines
02 May - 04 May Frontier Airlines
11 May - 15 May Frontier Airlines
30 May - 06 Jun Frontier Airlines
31 May - 02 Jun Frontier Airlines
25 May - 01 Jun Frontier Airlines
28 May - 01 Jun Frontier Airlines
24 May - 08 Jun Frontier Airlines
29 May - 07 Jun Frontier Airlines
30 May - 03 Jun Frontier Airlines
31 May - 03 Jun Frontier Airlines
22 May - 22 Jun Frontier Airlines
27 May - 07 Jun Porter Airlines (Canada) Ltd

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

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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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