Flights from Chicago to Islita

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.

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$596 Roundtrip, found 16 hours ago

$596

Roundtrip

found 16 hours ago

Select American Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $596 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$601 Roundtrip, found 16 hours ago

$601

Roundtrip

found 16 hours ago

Select American Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $601 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$626 Roundtrip, found 16 hours ago

$626

Roundtrip

found 16 hours ago

Select United flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $626 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$627 Roundtrip, found 16 hours ago

$627

Roundtrip

found 16 hours ago

Select Copa flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $627 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$635 Roundtrip, found 16 hours ago

$635

Roundtrip

found 16 hours ago

Select Copa flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $635 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$638 Roundtrip, found 16 hours ago

$638

Roundtrip

found 16 hours ago

Select avianca flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $638 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$651 Roundtrip, found 16 hours ago

$651

Roundtrip

found 16 hours ago

Select United flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $651 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$662 Roundtrip, found 16 hours ago

$662

Roundtrip

found 16 hours ago

Select American Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $662 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$665 Roundtrip, found 16 hours ago

$665

Roundtrip

found 16 hours ago

Select Copa flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $665 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$671 Roundtrip, found 16 hours ago

$671

Roundtrip

found 16 hours ago

Select American Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $671 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$676 Roundtrip, found 16 hours ago

$676

Roundtrip

found 16 hours ago

Select United flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $676 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$680 Roundtrip, found 16 hours ago

$680

Roundtrip

found 16 hours ago

Select American Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $680 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$681 Roundtrip, found 16 hours ago

$681

Roundtrip

found 16 hours ago

Select American Airlines flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $681 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$702 Roundtrip, found 16 hours ago

$702

Roundtrip

found 16 hours ago

Select Copa flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $702 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$787 Roundtrip, found 16 hours ago

$787

Roundtrip

found 16 hours ago

Select avianca flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $787 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$822 Roundtrip, found 16 hours ago

$822

Roundtrip

found 16 hours ago

Select United flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $822 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$926 Roundtrip, found 16 hours ago

$926

Roundtrip

found 16 hours ago

Select Delta flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $926 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$1,021 Roundtrip, found 16 hours ago

$1,021

Roundtrip

found 16 hours ago

Select JetBlue Airways flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $1,021 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$1,048 Roundtrip, found 16 hours ago

$1,048

Roundtrip

found 16 hours ago

Select Air Canada flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $1,048 found 16 hours ago

Fri, Jan 2 - Wed, Jan 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$1,462 Roundtrip, found 16 hours ago

$1,462

Roundtrip

found 16 hours ago

Select Aeromexico flight, departing Fri, Jan 2 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jan 7, priced at $1,462 found 16 hours ago