Our cheapest offers for flights from Chicago O'Hare to Puerto Rico

Here you can compare cheap flights from Chicago O'Hare (ORD) 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 O'Hare (ORD) to San Juan (Puerto Rico) (SJU)

	Outbound	Return	Airlines	Baggage	Price
Chicago O'Hare San Juan (Puerto Rico)	Outbound 04/21/25 2 Stopovers (ATL, MCO) F91596, F94556, F94726 39h 29min	Return 05/19/25 2 Stopovers (BWI, ATL) F92265, F92509, F91595 35h 43min	Frontier Airlines	?	$197 found 3 days ago
Best option Chicago O'Hare San Juan (Puerto Rico)	Outbound 06/20/25 direct AA2852 04h 45min	Return 07/19/25 direct AA1184 05h 10min	American Airlines	?	$465
Chicago O'Hare San Juan (Puerto Rico)	Outbound 04/21/25 1 Stopover (MCO) NK1506, NK0980 08h 57min	Return 05/19/25 1 Stopover (ATL) F92871, F93397 13h 25min	Spirit Airlines		$239 found 3 days ago