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Our cheapest offers for flights from Chicago to Puerto Rico

Here you can compare cheap flights from Chicago (CHI) to Puerto Rico for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Puerto Rico. Prices and availability may change at any time.

Flights from Chicago (CHI) to San Juan (Puerto Rico) (SJU)

	Outbound	Return	Airlines	Baggage	Price
Chicago San Juan (Puerto Rico)	Outbound 02/19/25 1 Stopover (MIA) NK1843, NK1193 08h 38min	Return 03/10/25 1 Stopover (CLT) AA2218, AA1668 17h 21min	Spirit Airlines	?	$325
Best option Chicago San Juan (Puerto Rico)	Outbound 03/02/25 direct NK0491 04h 47min	Return 03/07/25 direct UA2088 05h 21min	Spirit Airlines	?	$405
Chicago San Juan (Puerto Rico)	Outbound 12/13/24 1 Stopover (MCO) F93044, F92250 16h 09min	Return 12/31/24 1 Stopover (ATL) F92081, AA0780 11h 54min	Frontier Airlines	?	$373