Flights from Chicago to South Bay

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.

Wed, Jul 16 - Tue, Jul 22

ORD

O'Hare Intl.

SAN

San Diego Intl.

$167 Roundtrip, found 2 days ago

$167

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to San Diego Intl., returning Tue, Jul 22, priced at $167 found 2 days ago

Tue, Jul 22 - Wed, Jul 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$186 Roundtrip, found 2 days ago

$186

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to San Diego Intl., returning Wed, Jul 23, priced at $186 found 2 days ago

Wed, Jul 16 - Sat, Jul 19

ORD

O'Hare Intl.

SAN

San Diego Intl.

$203 Roundtrip, found 2 days ago

$203

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to San Diego Intl., returning Sat, Jul 19, priced at $203 found 2 days ago

Sun, Aug 10 - Fri, Aug 15

ORD

O'Hare Intl.

SAN

San Diego Intl.

$205 Roundtrip, found 2 days ago

$205

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sun, Aug 10 from O'Hare Intl. to San Diego Intl., returning Fri, Aug 15, priced at $205 found 2 days ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

SAN

San Diego Intl.

$206 Roundtrip, found 2 days ago

$206

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to San Diego Intl., returning Wed, Aug 13, priced at $206 found 2 days ago

Thu, Jul 17 - Tue, Jul 22

ORD

O'Hare Intl.

SAN

San Diego Intl.

$223 Roundtrip, found 2 days ago

$223

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Jul 17 from O'Hare Intl. to San Diego Intl., returning Tue, Jul 22, priced at $223 found 2 days ago

Sat, Jul 19 - Thu, Jul 24

ORD

O'Hare Intl.

SAN

San Diego Intl.

$224 Roundtrip, found 2 days ago

$224

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to San Diego Intl., returning Thu, Jul 24, priced at $224 found 2 days ago

Thu, Aug 7 - Sat, Aug 9

ORD

O'Hare Intl.

SAN

San Diego Intl.

$225 Roundtrip, found 2 days ago

$225

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Aug 7 from O'Hare Intl. to San Diego Intl., returning Sat, Aug 9, priced at $225 found 2 days ago

Tue, Jul 22 - Sun, Jul 27

ORD

O'Hare Intl.

SAN

San Diego Intl.

$227 Roundtrip, found 3 days ago

$227

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to San Diego Intl., returning Sun, Jul 27, priced at $227 found 3 days ago

Wed, Jul 16 - Sun, Jul 20

ORD

O'Hare Intl.

SAN

San Diego Intl.

$228 Roundtrip, found 2 days ago

$228

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to San Diego Intl., returning Sun, Jul 20, priced at $228 found 2 days ago

Thu, Jul 17 - Mon, Jul 21

ORD

O'Hare Intl.

SAN

San Diego Intl.

$232 Roundtrip, found 2 days ago

$232

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Jul 17 from O'Hare Intl. to San Diego Intl., returning Mon, Jul 21, priced at $232 found 2 days ago

Sat, Jul 19 - Sun, Jul 20

ORD

O'Hare Intl.

SAN

San Diego Intl.

$233 Roundtrip, found 2 days ago

$233

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to San Diego Intl., returning Sun, Jul 20, priced at $233 found 2 days ago

Tue, Jul 22 - Sun, Jul 27

ORD

O'Hare Intl.

SAN

San Diego Intl.

$236 Roundtrip, found 3 days ago

$236

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to San Diego Intl., returning Sun, Jul 27, priced at $236 found 3 days ago

Tue, Jul 22 - Sun, Jul 27

ORD

O'Hare Intl.

SAN

San Diego Intl.

$237 Roundtrip, found 3 days ago

$237

Roundtrip

found 3 days ago

Select United flight, departing Tue, Jul 22 from O'Hare Intl. to San Diego Intl., returning Sun, Jul 27, priced at $237 found 3 days ago

Tue, Aug 12 - Tue, Aug 12

ORD

O'Hare Intl.

SAN

San Diego Intl.

$246 Roundtrip, found 2 days ago

$246

Roundtrip

found 2 days ago

Select American Airlines flight, departing Tue, Aug 12 from O'Hare Intl. to San Diego Intl., returning Tue, Aug 12, priced at $246 found 2 days ago

Sat, Nov 15 - Thu, Nov 27

ORD

O'Hare Intl.

SAN

San Diego Intl.

$267 Roundtrip, found 1 day ago

$267

Roundtrip

found 1 day ago

Select Hawaiian Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to San Diego Intl., returning Thu, Nov 27, priced at $267 found 1 day ago

Tue, Jun 24 - Tue, Jul 1

MDW

Midway Intl.

SAN

San Diego Intl.

$270 Roundtrip, found 3 days ago

$270

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Jun 24 from Midway Intl. to San Diego Intl., returning Tue, Jul 1, priced at $270 found 3 days ago

Sat, Nov 15 - Thu, Nov 27

MDW

Midway Intl.

SAN

San Diego Intl.

$287 Roundtrip, found 17 hours ago

$287

Roundtrip

found 17 hours ago

Select Delta flight, departing Sat, Nov 15 from Midway Intl. to San Diego Intl., returning Thu, Nov 27, priced at $287 found 17 hours ago

Tue, Jul 22 - Sun, Jul 27

ORD

O'Hare Intl.

CLD

McClellan-Palomar

$341 Roundtrip, found 3 days ago

$341

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to McClellan-Palomar, returning Sun, Jul 27, priced at $341 found 3 days ago

Tue, Jul 22 - Sun, Jul 27

ORD

O'Hare Intl.

SAN

San Diego Intl.

$457 Roundtrip, found 3 days ago

$457

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to San Diego Intl., returning Sun, Jul 27, priced at $457 found 3 days ago