Cheap flights from Chicago to Caribbean Coast

View NZ$424 flight on Sat, 16 Aug. 2025Opens in a new window

Popular airlines from Chicago to Caribbean Coast

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Cheap Flights from Chicago (CHI) to Caribbean Coast (SJO)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

avianca
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
SJO
San José
NZ$617 Return, found 5 days ago
NZ$617
Return
found 5 days ago
Select avianca flight, departing Sat, 16 Aug. from Chicago to San José, returning Sat, 23 Aug., priced at NZ$617 found 5 days ago
avianca
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
SJO
San José
NZ$742 Return, found 5 days ago
NZ$742
Return
found 5 days ago
Select avianca flight, departing Sat, 16 Aug. from Chicago to San José, returning Sat, 23 Aug., priced at NZ$742 found 5 days ago
American Airlines
Wed, 20 Aug. - Wed, 27 Aug.
ORD
Chicago
SJO
San José
NZ$762 Return, found 2 days ago
NZ$762
Return
found 2 days ago
Select American Airlines flight, departing Wed, 20 Aug. from Chicago to San José, returning Wed, 27 Aug., priced at NZ$762 found 2 days ago
Copa
Sat, 16 Aug. - Sat, 23 Aug.
ORD
Chicago
SJO
San José
NZ$795 Return, found 5 days ago
NZ$795
Return
found 5 days ago
Select Copa flight, departing Sat, 16 Aug. from Chicago to San José, returning Sat, 23 Aug., priced at NZ$795 found 5 days ago
Air Canada
Wed, 20 Aug. - Wed, 27 Aug.
ORD
Chicago
SJO
San José
NZ$831 Return, found 2 days ago
NZ$831
Return
found 2 days ago
Select Air Canada flight, departing Wed, 20 Aug. from Chicago to San José, returning Wed, 27 Aug., priced at NZ$831 found 2 days ago
United
Tue, 12 Aug. - Fri, 22 Aug.
ORD
Chicago
SJO
San José
NZ$981 Return, found 19 hours ago
NZ$981
Return
found 19 hours ago
Select United flight, departing Tue, 12 Aug. from Chicago to San José, returning Fri, 22 Aug., priced at NZ$981 found 19 hours ago
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