Cheapest return flights from Chicago to San Juan in May from $198

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

Return flights

11 May - 14 May Frontier Airlines
02 May - 04 May Frontier Airlines
07 May - 11 May Frontier Airlines
14 May - 18 May Frontier Airlines
13 May - 18 May Frontier Airlines
06 May - 11 May Frontier Airlines
02 May - 08 May Frontier Airlines
06 May - 14 May Spirit Airlines
13 May - 14 May Spirit Airlines
03 May - 14 May Spirit Airlines
19 May - 03 Jun Spirit Airlines
19 May - 02 Jun Spirit Airlines
31 May - 03 Jun Spirit Airlines
31 May - 02 Jun Spirit Airlines
27 May - 03 Jun Spirit Airlines
13 May - 02 Jun Spirit Airlines
28 May - 02 Jun Spirit Airlines
19 May - 03 Jun Spirit Airlines direct
31 May - 13 Jun Spirit Airlines direct
31 May - 03 Jun Spirit Airlines direct

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

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