Cheapest one-way flights from Chicago to San Juan in May from $77

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

One-Way flights

16 May Frontier Airlines
06 May Frontier Airlines
09 May Frontier Airlines
19 May Spirit Airlines direct
31 May Spirit Airlines direct
06 May Spirit Airlines direct
11 May Spirit Airlines direct
03 May Spirit Airlines direct
28 May Spirit Airlines direct
02 May Frontier Airlines

Also check the deals for return flights from Chicago to San Juan in May.

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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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