Cheapest return flights from Chicago to San Juan in May from $201

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

Return flights

03 May - 06 May Frontier Airlines
01 May - 03 May Frontier Airlines
10 May - 14 May Frontier Airlines
02 May - 09 May Frontier Airlines
08 May - 13 May Frontier Airlines
11 May - 16 May Frontier Airlines
08 May - 11 May Frontier Airlines
03 May - 16 May Frontier Airlines
12 May - 16 May Southwest Airlines
08 May - 10 May Frontier Airlines
27 May - 02 Jun Southwest Airlines
30 May - 02 Jun Southwest Airlines
29 May - 02 Jun Southwest Airlines
18 May - 01 Jun Southwest Airlines
31 May - 03 Jun Southwest Airlines
27 May - 03 Jun Southwest Airlines
30 May - 06 Jun Southwest Airlines

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

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