Cheapest return flights from Chicago to San Juan in May from $176

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

19 May - 29 May Spirit Airlines
03 May - 10 May Spirit Airlines
25 May - 29 May Spirit Airlines
10 May - 11 May Spirit Airlines
19 May - 24 May Spirit Airlines
17 May - 24 May Spirit Airlines
09 May - 11 May Spirit Airlines direct
12 May - 16 May Spirit Airlines direct
29 May - 02 Jun Spirit Airlines
30 May - 02 Jun Spirit Airlines
17 May - 22 May Spirit Airlines
03 May - 09 May Spirit Airlines
30 May - 06 Jun Spirit Airlines
26 May - 03 Jun Spirit Airlines direct
27 May - 03 Jun Spirit Airlines direct
27 May - 07 Jun Spirit Airlines
31 May - 02 Jun Spirit Airlines
31 May - 03 Jun Spirit Airlines
28 May - 01 Jun Spirit Airlines
24 May - 08 Jun Spirit Airlines

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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