Cheap flights from Chicago to Caribbean Coast

View AU$304 flight on Wed, 3 Sep. 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.

Copa
Thu, 6 Nov. - Tue, 18 Nov.
ORD
Chicago
SJO
San José
AU$648 Return, found 1 day ago
AU$648
Return
found 1 day ago
Select Copa flight, departing Thu, 6 Nov. from Chicago to San José, returning Tue, 18 Nov., priced at AU$648 found 1 day ago
Copa
Mon, 3 Nov. - Tue, 18 Nov.
ORD
Chicago
SJO
San José
AU$671 Return, found 1 day ago
AU$671
Return
found 1 day ago
Select Copa flight, departing Mon, 3 Nov. from Chicago to San José, returning Tue, 18 Nov., priced at AU$671 found 1 day ago
Air Canada
Tue, 4 Nov. - Mon, 17 Nov.
ORD
Chicago
SJO
San José
AU$755 Return, found 1 day ago
AU$755
Return
found 1 day ago
Select Air Canada flight, departing Tue, 4 Nov. from Chicago to San José, returning Mon, 17 Nov., priced at AU$755 found 1 day ago
American Airlines
Wed, 3 Sep. - Wed, 10 Sep.
ORD
Chicago
SJO
San José
AU$778 Return, found 5 days ago
AU$778
Return
found 5 days ago
Select American Airlines flight, departing Wed, 3 Sep. from Chicago to San José, returning Wed, 10 Sep., priced at AU$778 found 5 days ago
United
Wed, 3 Sep. - Wed, 10 Sep.
ORD
Chicago
SJO
San José
AU$786 Return, found 5 days ago
AU$786
Return
found 5 days ago
Select United flight, departing Wed, 3 Sep. from Chicago to San José, returning Wed, 10 Sep., priced at AU$786 found 5 days ago
Delta
Mon, 8 Dec. - Sat, 27 Dec.
ORD
Chicago
SJO
San José
AU$1,062 Return, found 1 day ago
AU$1,062
Return
found 1 day ago
Select Delta flight, departing Mon, 8 Dec. from Chicago to San José, returning Sat, 27 Dec., priced at AU$1,062 found 1 day ago
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