Chicago to Caribbean Coast Flights (CHI-SJO) from $81

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Selected fares from Chicago to Caribbean Coast

The cheapest prices found with in the last 7 days for return flights were $190 and $81 for one-way flights to Caribbean Coast for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Sep 10 - Wed, Sep 18
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$190 Roundtrip, found 9 hours ago
$190
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Tue, Sep 10 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Sep 18, priced at $190 found 9 hours ago
avianca
Wed, Jan 15 - Wed, Jan 22
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$308 Roundtrip, found 1 day ago
$308
Roundtrip
found 1 day ago
Select avianca flight, departing Wed, Jan 15 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 22, priced at $308 found 1 day ago
Frontier Airlines
Wed, Jul 17 - Thu, Jul 25
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$335 Roundtrip, found 3 days ago
$335
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Jul 17 from O'Hare Intl. to Juan Santamaría Intl., returning Thu, Jul 25, priced at $335 found 3 days ago

Save more with Caribbean Coast Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Studio Hotel Boutique

Studio Hotel Boutique

4 out of 5
per person
Jul 11 - Jul 15
found 2 days ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
Barceló Tambor - All Inclusive

Barceló Tambor - All Inclusive

4 out of 5
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
Xandari Resort And Spa

Xandari Resort And Spa

3.5 out of 5
per person
Jul 11 - Jul 15
found 2 days ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
Montaña de Fuego All Inclusive

Montaña de Fuego All Inclusive

3 out of 5
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
Finca Rosa Blanca Coffee Farm and Inn

Finca Rosa Blanca Coffee Farm and Inn

4 out of 5
per person
Jul 11 - Jul 15
found 2 days ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
Hotel Pico Colorado

Hotel Pico Colorado

2 out of 5
per person
Jul 11 - Jul 15
found 2 days ago
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
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