Cheapest return flights from Chicago to San Juan in May from $202

AirHint found the following cheapest return flights from Chicago (MDW) to San Juan (SJU) in May 2026 (see full year).

Return flights

10 May - 14 May Frontier Airlines
04 May - 09 May Frontier Airlines
15 May - 17 May Frontier Airlines
01 May - 08 May Frontier Airlines
14 May - 17 May Frontier Airlines
28 May - 30 May Frontier Airlines
01 May - 03 May Frontier Airlines
28 May - 01 Jun Frontier Airlines
06 May - 09 May Delta
08 May - 11 May Frontier Airlines
08 May - 08 May Frontier Airlines
28 May - 02 Jun Frontier Airlines
29 May - 02 Jun Frontier Airlines
28 May - 03 Jun Frontier Airlines
29 May - 03 Jun Frontier Airlines
30 May - 04 Jun Frontier Airlines
27 May - 02 Jun Delta
19 May - 02 Jun Southwest Airlines
30 May - 03 Jun Southwest Airlines
26 May - 03 Jun Southwest Airlines

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

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