Flights from Chicago to San Mateo

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.

Mon, Jun 30 - Tue, Jul 8

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$365 Roundtrip, found 2 days ago

$365

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jun 30 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jul 8, priced at $365 found 2 days ago

Mon, Jun 30 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$374 Roundtrip, found 2 days ago

$374

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jun 30 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $374 found 2 days ago

Tue, Jul 1 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$380 Roundtrip, found 2 days ago

$380

Roundtrip

found 2 days ago

Select avianca flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $380 found 2 days ago

Mon, Jun 30 - Wed, Jul 9

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$383 Roundtrip, found 2 days ago

$383

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jun 30 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jul 9, priced at $383 found 2 days ago

Tue, Jul 1 - Tue, Jul 8

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$390 Roundtrip, found 2 days ago

$390

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jul 8, priced at $390 found 2 days ago

Mon, Jun 30 - Tue, Jul 8

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$395 Roundtrip, found 2 days ago

$395

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jun 30 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jul 8, priced at $395 found 2 days ago

Tue, Jul 1 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$397 Roundtrip, found 2 days ago

$397

Roundtrip

found 2 days ago

Select avianca flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $397 found 2 days ago

Tue, Jul 1 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$398 Roundtrip, found 2 days ago

$398

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $398 found 2 days ago

Tue, Jul 1 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$399 Roundtrip, found 2 days ago

$399

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $399 found 2 days ago

Sat, Jun 28 - Tue, Jul 8

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$400 Roundtrip, found 2 days ago

$400

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jul 8, priced at $400 found 2 days ago

Mon, Jun 30 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$404 Roundtrip, found 2 days ago

$404

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jun 30 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $404 found 2 days ago

Tue, Jul 1 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$404 Roundtrip, found 2 days ago

$404

Roundtrip

found 2 days ago

Select avianca flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $404 found 2 days ago

Tue, Jul 1 - Wed, Jul 9

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$408 Roundtrip, found 2 days ago

$408

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jul 9, priced at $408 found 2 days ago

Mon, Jun 30 - Wed, Jul 9

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$413 Roundtrip, found 2 days ago

$413

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Jun 30 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jul 9, priced at $413 found 2 days ago

Tue, Jul 1 - Sun, Jul 6

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$416 Roundtrip, found 2 days ago

$416

Roundtrip

found 2 days ago

Select avianca flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Sun, Jul 6, priced at $416 found 2 days ago

Sun, Jun 29 - Tue, Jul 8

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$418 Roundtrip, found 2 days ago

$418

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Jun 29 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jul 8, priced at $418 found 2 days ago

Sat, Jun 28 - Wed, Jul 9

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$418 Roundtrip, found 2 days ago

$418

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jun 28 from O'Hare Intl. to Juan Santamaría Intl., returning Wed, Jul 9, priced at $418 found 2 days ago

Tue, Jul 1 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$614 Roundtrip, found 2 days ago

$614

Roundtrip

found 2 days ago

Select American Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $614 found 2 days ago

Tue, Jul 1 - Mon, Jul 7

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$1,018 Roundtrip, found 2 days ago

$1,018

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jul 7, priced at $1,018 found 2 days ago

Tue, Jul 1 - Sun, Jul 6

ORD

O'Hare Intl.

SJO

Juan Santamaría Intl.

$3,604 Roundtrip, found 2 days ago

$3,604

Roundtrip

found 2 days ago

Select Air Canada flight, departing Tue, Jul 1 from O'Hare Intl. to Juan Santamaría Intl., returning Sun, Jul 6, priced at $3,604 found 2 days ago