Flights from Chicago to San José del Cabo

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, Jul 29 - Thu, Aug 14

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$390 Roundtrip, found 3 days ago

$390

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Los Cabos Intl., returning Thu, Aug 14, priced at $390 found 3 days ago

Wed, Jul 30 - Thu, Aug 14

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$390 Roundtrip, found 3 days ago

$390

Roundtrip

found 3 days ago

Select Aeromexico flight, departing Wed, Jul 30 from O'Hare Intl. to Los Cabos Intl., returning Thu, Aug 14, priced at $390 found 3 days ago

Tue, Jul 29 - Tue, Aug 12

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$400 Roundtrip, found 3 days ago

$400

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to Los Cabos Intl., returning Tue, Aug 12, priced at $400 found 3 days ago

Tue, Jul 29 - Fri, Aug 8

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$400 Roundtrip, found 3 days ago

$400

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Jul 29 from O'Hare Intl. to Los Cabos Intl., returning Fri, Aug 8, priced at $400 found 3 days ago

Sat, Aug 2 - Thu, Aug 14

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$430 Roundtrip, found 3 days ago

$430

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Aug 2 from O'Hare Intl. to Los Cabos Intl., returning Thu, Aug 14, priced at $430 found 3 days ago

Sat, Aug 2 - Fri, Aug 8

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$440 Roundtrip, found 3 days ago

$440

Roundtrip

found 3 days ago

Select Aeromexico flight, departing Sat, Aug 2 from O'Hare Intl. to Los Cabos Intl., returning Fri, Aug 8, priced at $440 found 3 days ago

Tue, Jul 29 - Sun, Aug 10

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$444 Roundtrip, found 3 days ago

$444

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Tue, Jul 29 from O'Hare Intl. to Los Cabos Intl., returning Sun, Aug 10, priced at $444 found 3 days ago

Sat, Aug 2 - Sun, Aug 10

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$450 Roundtrip, found 3 days ago

$450

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Los Cabos Intl., returning Sun, Aug 10, priced at $450 found 3 days ago

Fri, Aug 1 - Tue, Aug 12

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$452 Roundtrip, found 3 days ago

$452

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Los Cabos Intl., returning Tue, Aug 12, priced at $452 found 3 days ago

Sat, Aug 2 - Tue, Aug 5

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$453 Roundtrip, found 3 days ago

$453

Roundtrip

found 3 days ago

Select Aeromexico flight, departing Sat, Aug 2 from O'Hare Intl. to Los Cabos Intl., returning Tue, Aug 5, priced at $453 found 3 days ago

Sat, Aug 2 - Sun, Aug 10

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$457 Roundtrip, found 3 days ago

$457

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Los Cabos Intl., returning Sun, Aug 10, priced at $457 found 3 days ago

Fri, Aug 1 - Fri, Aug 8

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$462 Roundtrip, found 3 days ago

$462

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Los Cabos Intl., returning Fri, Aug 8, priced at $462 found 3 days ago

Mon, Aug 4 - Fri, Aug 8

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$464 Roundtrip, found 3 days ago

$464

Roundtrip

found 3 days ago

Select American Airlines flight, departing Mon, Aug 4 from O'Hare Intl. to Los Cabos Intl., returning Fri, Aug 8, priced at $464 found 3 days ago

Sun, Aug 3 - Fri, Aug 8

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$468 Roundtrip, found 3 days ago

$468

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sun, Aug 3 from O'Hare Intl. to Los Cabos Intl., returning Fri, Aug 8, priced at $468 found 3 days ago

Wed, Jul 30 - Sun, Aug 10

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$474 Roundtrip, found 3 days ago

$474

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Los Cabos Intl., returning Sun, Aug 10, priced at $474 found 3 days ago

Fri, Aug 1 - Sat, Aug 9

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$491 Roundtrip, found 3 days ago

$491

Roundtrip

found 3 days ago

Select United flight, departing Fri, Aug 1 from O'Hare Intl. to Los Cabos Intl., returning Sat, Aug 9, priced at $491 found 3 days ago

Fri, Aug 1 - Sat, Aug 9

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$515 Roundtrip, found 3 days ago

$515

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Los Cabos Intl., returning Sat, Aug 9, priced at $515 found 3 days ago

Sat, Aug 2 - Sun, Aug 10

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$598 Roundtrip, found 3 days ago

$598

Roundtrip

found 3 days ago

Select Volaris flight, departing Sat, Aug 2 from O'Hare Intl. to Los Cabos Intl., returning Sun, Aug 10, priced at $598 found 3 days ago

Fri, Aug 1 - Sat, Aug 9

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$663 Roundtrip, found 3 days ago

$663

Roundtrip

found 3 days ago

Select Viva Aerobus flight, departing Fri, Aug 1 from O'Hare Intl. to Los Cabos Intl., returning Sat, Aug 9, priced at $663 found 3 days ago

Fri, Aug 1 - Sat, Aug 9

ORD

O'Hare Intl.

SJD

Los Cabos Intl.

$934 Roundtrip, found 3 days ago

$934

Roundtrip

found 3 days ago

Select American Airlines flight, departing Fri, Aug 1 from O'Hare Intl. to Los Cabos Intl., returning Sat, Aug 9, priced at $934 found 3 days ago