Cheapest return ORD–SJU flights, May

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

Return flights

17 May - 22 May Frontier Airlines
13 May - 22 May Frontier Airlines
18 May - 22 May Frontier Airlines
08 May - 13 May Frontier Airlines
16 May - 23 May Frontier Airlines
17 May - 23 May Frontier Airlines
04 May - 08 May Spirit Airlines
05 May - 16 May Spirit Airlines
15 May - 22 May Frontier Airlines
16 May - 22 May Frontier Airlines
15 May - 05 Jun Spirit Airlines direct
17 May - 05 Jun Spirit Airlines direct
18 May - 05 Jun Spirit Airlines direct
16 May - 05 Jun Spirit Airlines direct
29 May - 06 Jun Spirit Airlines
30 May - 03 Jun Frontier Airlines
28 May - 04 Jun Frontier Airlines direct
19 May - 16 Jun Frontier Airlines
28 May - 01 Jun Frontier Airlines
21 May - 11 Jun Spirit Airlines direct

Also check the deals for one-way 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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