Flights from Chicago to San Juan

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.

Tue, Jun 17 - Fri, Jun 20

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$300 Roundtrip, found 1 day ago

$300

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Juan Santamaría Intl., returning Fri, Jun 20, priced at $300 found 1 day ago

Tue, Jun 17 - Tue, Jun 24

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$304 Roundtrip, found 1 day ago

$304

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jun 24, priced at $304 found 1 day ago

Tue, Jun 17 - Mon, Jun 23

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$314 Roundtrip, found 1 day ago

$314

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jun 23, priced at $314 found 1 day ago

Tue, Jun 17 - Thu, Jun 19

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$323 Roundtrip, found 1 day ago

$323

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Juan Santamaría Intl., returning Thu, Jun 19, priced at $323 found 1 day ago

Thu, Jun 12 - Fri, Jun 20

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$330 Roundtrip, found 1 day ago

$330

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Thu, Jun 12 from O'Hare Intl. to Juan Santamaría Intl., returning Fri, Jun 20, priced at $330 found 1 day ago

Sat, Jun 14 - Fri, Jun 20

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$334 Roundtrip, found 1 day ago

$334

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Fri, Jun 20, priced at $334 found 1 day ago

Sat, Jun 14 - Tue, Jun 24

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$339 Roundtrip, found 1 day ago

$339

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jun 24, priced at $339 found 1 day ago

Sun, Jun 15 - Fri, Jun 20

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$344 Roundtrip, found 1 day ago

$344

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Jun 15 from O'Hare Intl. to Juan Santamaría Intl., returning Fri, Jun 20, priced at $344 found 1 day ago

Sat, Jun 14 - Mon, Jun 23

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$348 Roundtrip, found 1 day ago

$348

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jun 23, priced at $348 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$349 Roundtrip, found 1 day ago

$349

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $349 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$352 Roundtrip, found 1 day ago

$352

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $352 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$448 Roundtrip, found 1 day ago

$448

Roundtrip

found 1 day ago

Select avianca flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $448 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$482 Roundtrip, found 1 day ago

$482

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $482 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$539 Roundtrip, found 1 day ago

$539

Roundtrip

found 1 day ago

Select United flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $539 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$548 Roundtrip, found 1 day ago

$548

Roundtrip

found 1 day ago

Select Copa flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $548 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$558 Roundtrip, found 1 day ago

$558

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $558 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$654 Roundtrip, found 1 day ago

$654

Roundtrip

found 1 day ago

Select Air Canada flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $654 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$800 Roundtrip, found 1 day ago

$800

Roundtrip

found 1 day ago

Select United flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $800 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$806 Roundtrip, found 1 day ago

$806

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $806 found 1 day ago

Sat, Jun 14 - Sat, Jun 21

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$940 Roundtrip, found 1 day ago

$940

Roundtrip

found 1 day ago

Select Aeromexico flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $940 found 1 day ago