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 $200 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, Aug 27 - Wed, Sep 4
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$200 Roundtrip, found 1 hour ago
$200
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Aug 27 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Sep 4, priced at $200 found 1 hour ago
Frontier Airlines
Wed, May 15 - Sun, May 19
MDW
Midway Intl.
SJO
Juan Santamaría Intl.
$283 Roundtrip, found 5 days ago
$283
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 15 from Midway Intl. to Juan Santamaría Intl., returning Sun, May 19, priced at $283 found 5 days ago
avianca
Wed, Jan 15 - Wed, Jan 22
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$318 Roundtrip, found 1 hour ago
$318
Roundtrip
found 1 hour ago
Select avianca flight, departing Wed, Jan 15 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 22, priced at $318 found 1 hour ago

Save more with Caribbean Coast Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Avita Lodge Hotel de Montaña

Avita Lodge Hotel de Montaña

2.5 out of 5
per person
Jun 12 - Jun 18
Roundtrip non-stop flight included
Chicago (ORD) to San José (SJO)
Hotel Cultura Plaza

Hotel Cultura Plaza

3 out of 5
per person
Jun 12 - Jun 18
Roundtrip non-stop flight included
Chicago (ORD) to San José (SJO)
Xandari Resort And Spa

Xandari Resort And Spa

3.5 out of 5
per person
Jun 24 - Jun 28
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
Arenal Sloth Hostel

Arenal Sloth Hostel

1 out of 5
per person
Jun 12 - Jun 18
Roundtrip non-stop flight included
Chicago (ORD) to San José (SJO)
Apartamentos Cityzen

Apartamentos Cityzen

4 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to San José (SJO)
Trapp Family Country Inn

Trapp Family Country Inn

3 out of 5
per person
Jun 17 - Jun 22
Roundtrip non-stop flight included
Chicago (ORD) to San José (SJO)
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