Cheapest return flights from Chicago to San Juan in May from $181

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

Return flights

06 May - 11 May jetBlue
02 May - 08 May jetBlue
16 May - 19 May jetBlue
01 May - 08 May jetBlue
09 May - 16 May jetBlue
15 May - 19 May jetBlue
07 May - 10 May jetBlue
02 May - 05 May Spirit Airlines
02 May - 19 May Spirit Airlines
02 May - 06 May Spirit Airlines
20 May - 10 Jun Spirit Airlines
16 May - 03 Jun Spirit Airlines
13 May - 03 Jun Spirit Airlines
14 May - 03 Jun Spirit Airlines
20 May - 03 Jun Spirit Airlines
16 May - 03 Jun Spirit Airlines direct
14 May - 03 Jun Spirit Airlines direct
20 May - 03 Jun Spirit Airlines direct
29 May - 10 Jun Spirit Airlines
15 May - 03 Jun Spirit Airlines

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

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