Our cheapest offers for flights from Chicago to Costa Rica

Here you can compare cheap flights from Chicago (CHI) to Costa Rica 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 Costa Rica. Prices and availability may change at any time.

Flights from Chicago (CHI) to San Jose, Costa Rica (SJO)

	Outbound	Return	Airlines	Baggage	Price
Chicago San Jose, Costa Rica	Outbound 04/21/25 3 Stopovers (MCO, ATL, FLL) NK0573, NK0211, NK0442, NK0335 27h 35min	Return 05/19/25 2 Stopovers (MCO, IAH) NK1310, NK1576, NK1145 21h 27min	Spirit Airlines	?	$339 found 3 days ago
Best option Chicago San Jose, Costa Rica	Outbound 06/20/25 1 Stopover (GUA) AV0631, AV0651 08h 30min	Return 07/19/25 1 Stopover (GDL) Q64058, Y41704 18h 33min	Avianca		$356
Chicago San Jose, Costa Rica Pay attention to transfer at connecting flight	Outbound 04/21/25 3 Stopovers (MCO, ATL, FLL) NK0573, NK0211, NK0681, NK0335 27h 35min	Return 05/19/25 3 Stopovers (MCO, IAH, FLL) NK1310, NK1576, NK0221, NK1026 26h 56min	Spirit Airlines		$365 found 3 days ago