Flights from Chicago to San Isidro

Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$436 Roundtrip, found 9 hours ago

$436

Roundtrip

found 9 hours ago

Select United flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $436 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$449 Roundtrip, found 9 hours ago

$449

Roundtrip

found 9 hours ago

Select Delta flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $449 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$490 Roundtrip, found 9 hours ago

$490

Roundtrip

found 9 hours ago

Select avianca flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $490 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$494 Roundtrip, found 9 hours ago

$494

Roundtrip

found 9 hours ago

Select Delta flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $494 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$497 Roundtrip, found 9 hours ago

$497

Roundtrip

found 9 hours ago

Select United flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $497 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$511 Roundtrip, found 9 hours ago

$511

Roundtrip

found 9 hours ago

Select United flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $511 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$517 Roundtrip, found 9 hours ago

$517

Roundtrip

found 9 hours ago

Select Copa flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $517 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$519 Roundtrip, found 9 hours ago

$519

Roundtrip

found 9 hours ago

Select Delta flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $519 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$524 Roundtrip, found 9 hours ago

$524

Roundtrip

found 9 hours ago

Select United flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $524 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$526 Roundtrip, found 9 hours ago

$526

Roundtrip

found 9 hours ago

Select United flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $526 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$527 Roundtrip, found 9 hours ago

$527

Roundtrip

found 9 hours ago

Select JetBlue Airways flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $527 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$527 Roundtrip, found 9 hours ago

$527

Roundtrip

found 9 hours ago

Select Copa flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $527 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$533 Roundtrip, found 9 hours ago

$533

Roundtrip

found 9 hours ago

Select avianca flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $533 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$567 Roundtrip, found 9 hours ago

$567

Roundtrip

found 9 hours ago

Select American Airlines flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $567 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$576 Roundtrip, found 9 hours ago

$576

Roundtrip

found 9 hours ago

Select Delta flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $576 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$596 Roundtrip, found 9 hours ago

$596

Roundtrip

found 9 hours ago

Select American Airlines flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $596 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$746 Roundtrip, found 9 hours ago

$746

Roundtrip

found 9 hours ago

Select Copa flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $746 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$788 Roundtrip, found 9 hours ago

$788

Roundtrip

found 9 hours ago

Select JetBlue Airways flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $788 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$859 Roundtrip, found 9 hours ago

$859

Roundtrip

found 9 hours ago

Select Air Canada flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $859 found 9 hours ago

Sat, Feb 7 - Sat, Feb 14

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$940 Roundtrip, found 9 hours ago

$940

Roundtrip

found 9 hours ago

Select Aeromexico flight, departing Sat, Feb 7 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Feb 14, priced at $940 found 9 hours ago