Compare Chicago to Costa Rica flight deals starting at $349

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Find flights from Chicago (ORD) to Costa Rica

Chicago (ORD) to Liberia (Costa Rica) (LIR)

Depart Tue 6 Nov 2018,
Return Wed 21 Nov 2018
from$ 538*Viewed: 28 minutes ago

Chicago (ORD) to San Jose, CR (SJO)

Depart Thu 11 Oct 2018,
Return Fri 26 Oct 2018
from$ 349*Viewed: 28 minutes ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.
Coastline of Costa Rica with lush palm trees and jungle foliage on the sandy beach

Plan ahead for flights from Chicago to Costa Rica

from
to
Type
Dates
Price*
Chicago (ORD)
to San Jose, CR (SJO)
Roundtrip
Depart Tue 23 Oct 2018
Return Wed 7 Nov 2018
from$ 349*Viewed: 28 minutes ago
Chicago (ORD)
to Liberia (Costa Rica) (LIR)
Roundtrip
Depart Tue 13 Nov 2018
Return Wed 28 Nov 2018
from$ 538*Viewed: 28 minutes ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. Fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply.