Flights from Chicago to South San Diego

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.

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$122 Roundtrip, found 5 days ago

$122

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to San Diego Intl., returning Sat, Aug 23, priced at $122 found 5 days ago

Tue, Oct 7 - Tue, Oct 14

ORD

O'Hare Intl.

SAN

San Diego Intl.

$139 Roundtrip, found 3 days ago

$139

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Tue, Oct 7 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 14, priced at $139 found 3 days ago

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$141 Roundtrip, found 5 days ago

$141

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to San Diego Intl., returning Sat, Aug 23, priced at $141 found 5 days ago

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$148 Roundtrip, found 5 days ago

$148

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to San Diego Intl., returning Sat, Aug 23, priced at $148 found 5 days ago

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$148 Roundtrip, found 5 days ago

$148

Roundtrip

found 5 days ago

Select United flight, departing Sat, Aug 16 from O'Hare Intl. to San Diego Intl., returning Sat, Aug 23, priced at $148 found 5 days ago

Mon, Oct 6 - Tue, Oct 14

ORD

O'Hare Intl.

SAN

San Diego Intl.

$158 Roundtrip, found 3 days ago

$158

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Mon, Oct 6 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 14, priced at $158 found 3 days ago

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$160 Roundtrip, found 5 days ago

$160

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to San Diego Intl., returning Sat, Aug 23, priced at $160 found 5 days ago

Thu, Oct 9 - Tue, Oct 14

ORD

O'Hare Intl.

SAN

San Diego Intl.

$168 Roundtrip, found 3 days ago

$168

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Thu, Oct 9 from O'Hare Intl. to San Diego Intl., returning Tue, Oct 14, priced at $168 found 3 days ago

Fri, Aug 15 - Fri, Aug 22

ORD

O'Hare Intl.

SAN

San Diego Intl.

$169 Roundtrip, found 6 days ago

$169

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Fri, Aug 15 from O'Hare Intl. to San Diego Intl., returning Fri, Aug 22, priced at $169 found 6 days ago

Thu, Oct 9 - Fri, Oct 10

ORD

O'Hare Intl.

SAN

San Diego Intl.

$172 Roundtrip, found 3 days ago

$172

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Oct 9 from O'Hare Intl. to San Diego Intl., returning Fri, Oct 10, priced at $172 found 3 days ago

Mon, Oct 6 - Fri, Oct 10

ORD

O'Hare Intl.

SAN

San Diego Intl.

$177 Roundtrip, found 3 days ago

$177

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Mon, Oct 6 from O'Hare Intl. to San Diego Intl., returning Fri, Oct 10, priced at $177 found 3 days ago

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$178 Roundtrip, found 5 days ago

$178

Roundtrip

found 5 days ago

Select United flight, departing Sat, Aug 16 from O'Hare Intl. to San Diego Intl., returning Sat, Aug 23, priced at $178 found 5 days ago

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

SAN

San Diego Intl.

$182 Roundtrip, found 5 days ago

$182

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to San Diego Intl., returning Sat, Aug 23, priced at $182 found 5 days ago

Fri, Aug 15 - Fri, Aug 22

ORD

O'Hare Intl.

SAN

San Diego Intl.

$183 Roundtrip, found 6 days ago

$183

Roundtrip

found 6 days ago

Select United flight, departing Fri, Aug 15 from O'Hare Intl. to San Diego Intl., returning Fri, Aug 22, priced at $183 found 6 days ago

Mon, Oct 6 - Mon, Oct 13

ORD

O'Hare Intl.

SAN

San Diego Intl.

$187 Roundtrip, found 3 days ago

$187

Roundtrip

found 3 days ago

Select Hawaiian Airlines flight, departing Mon, Oct 6 from O'Hare Intl. to San Diego Intl., returning Mon, Oct 13, priced at $187 found 3 days ago

Fri, Aug 29 - Sun, Aug 31

ORD

O'Hare Intl.

SAN

San Diego Intl.

$188 Roundtrip, found 1 day ago

$188

Roundtrip

found 1 day ago

Select United flight, departing Fri, Aug 29 from O'Hare Intl. to San Diego Intl., returning Sun, Aug 31, priced at $188 found 1 day ago

Thu, Oct 9 - Mon, Oct 13

ORD

O'Hare Intl.

SAN

San Diego Intl.

$197 Roundtrip, found 3 days ago

$197

Roundtrip

found 3 days ago

Select Alaska Airlines flight, departing Thu, Oct 9 from O'Hare Intl. to San Diego Intl., returning Mon, Oct 13, priced at $197 found 3 days ago

Sat, Aug 16 - Sat, Aug 23

ORD

O'Hare Intl.

CLD

McClellan-Palomar

$213 Roundtrip, found 5 days ago

$213

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sat, Aug 16 from O'Hare Intl. to McClellan-Palomar, returning Sat, Aug 23, priced at $213 found 5 days ago

Wed, Aug 6 - Tue, Aug 12

MDW

Midway Intl.

SAN

San Diego Intl.

$248 Roundtrip, found 2 days ago

$248

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Wed, Aug 6 from Midway Intl. to San Diego Intl., returning Tue, Aug 12, priced at $248 found 2 days ago

Fri, Aug 29 - Sun, Aug 31

ORD

O'Hare Intl.

SAN

San Diego Intl.

$257 Roundtrip, found 1 day ago

$257

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 29 from O'Hare Intl. to San Diego Intl., returning Sun, Aug 31, priced at $257 found 1 day ago