Cheapest return flights from Chicago to San Juan in May from $212

Best time to book flights for Chicago (ORD) to San Juan (SJU) flights at AirHint

AirHint found the following cheapest return flights from Chicago (ORD) to San Juan (SJU) in May 2025 (see full year).

Return flights

05 May - 09 May Spirit Airlines direct
01 May - 01 May Spirit Airlines
05 May - 08 May Spirit Airlines direct
12 May - 16 May Spirit Airlines direct
19 May - 25 May Spirit Airlines direct
12 May - 15 May Frontier Airlines
08 May - 15 May Spirit Airlines
09 May - 16 May Spirit Airlines
04 May - 08 May Spirit Airlines direct
20 May - 25 May Spirit Airlines direct
29 May - 01 Jun Spirit Airlines direct
30 May - 06 Jun Spirit Airlines
27 May - 07 Jun Spirit Airlines
30 May - 03 Jun Spirit Airlines direct
26 May - 03 Jun Spirit Airlines direct
30 May - 02 Jun Spirit Airlines direct
29 May - 03 Jun Spirit Airlines direct
30 May - 01 Jun Spirit Airlines direct
29 May - 07 Jun Spirit Airlines
30 May - 08 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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