Cheapest one-way flights from Chicago to San Juan in May from 67€

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

One-Way flights

02 May Frontier Airlines
17 May Frontier Airlines
19 May Spirit Airlines
18 May Frontier Airlines
15 May Frontier Airlines
12 May Spirit Airlines
06 May Spirit Airlines
05 May Spirit Airlines
19 May Spirit Airlines direct
12 May Spirit Airlines direct

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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