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

Return flights

01 May - 05 May	jetBlue
08 May - 10 May	jetBlue
24 May - 30 May	American Airlines	direct
11 May - 17 May	American Airlines	direct
01 May - 05 May	American Airlines	direct
14 May - 18 May	United	direct
22 May - 29 May	jetBlue
21 May - 24 May	Southwest Airlines
21 May - 24 May	American Airlines	direct
22 May - 29 May	United	direct

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

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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Cheapest return flights from Chicago to San Juan in May from $344

Return flights